理学博士, 名古屋大学, 1979年03月

Ph. D, Nagoya University

Bioluminescence

Natural Products

Biological Organic Chemistry

生物発光

天然有機化合物

生物有機化学

ライフサイエンス, 生物有機化学

ナノテク・材料, 生体化学

ナノテク・材料, 生物分子化学

2019年04月 - 現在
電気通信大学, 脳・医工学研究センター, 客員教授

2013年04月 - 現在
電気通信大学, 名誉教授

2013年04月 - 2019年03月
電気通信大学, 脳科学ライフサポートセンター, 特任教授

2010年04月 - 2013年03月
電気通信大学, 大学院情報理工学研究科, 教授

1994年04月 - 2010年03月
電気通信大学, 電気通信学部, 教授

1984年03月 - 1994年03月
名古屋大学, 理学部, 助教授

1980年06月 - 1984年03月
名古屋大学, 理学部, 助手

1973年04月 - 1980年06月
小野薬品工業（株）, 中央研究所, 研究員

1971年04月 - 1973年03月
名古屋大学, 理学研究科, 化学専攻

1966年04月 - 1971年03月
名古屋大学, 理学部, 化学科

2001年 - 2003年
Assocate editor of Bull. Chem. Soc. Jpn., The Chemical Society of Japan, 学協会

2001年 - 2003年
欧文誌編集委員, 日本化学会, 学協会

1988年 - 1988年
Assocate editor of Bull. Chem. Soc. Jpn., The Chemical Society of Japan, 学協会

1988年 - 1988年
欧文誌編集委員, 日本化学会, 学協会

受賞日 1987年02月
有機合成化学奨励賞（有機合成化学協会）

Toward bioluminescence in the near-infrared region: Tuning the emission wavelength of firefly luciferin analogues by allyl substitution
Nobuo Kitada; Tsuyoshi Saitoh; Yuma Ikeda; Satoshi Iwano; Rika Obata; Haruki Niwa; Takashi Hirano; Atsushi Miyawaki; Koji Suzuki; Shigeru Nishiyama; Shojiro A. Maki
Tetrahedron Letters, Elsevier Ltd, 59巻, 12号, 掲載ページ 1087-1090, 出版日 2018年03月21日, 査読付, The synthesis and bioluminescence of allyl-substituted luciferin derivatives as substrates for firefly luciferase are reported. The allylation of luciferins induced bathochromic shift (15–40 nm) of the bioluminescence emission. Upon combination with other chemical modifications for bioluminescence wavelength tuning, novel red emitting luciferin analogues were obtained with emission maxima at 685 and 690 nm.
研究論文（学術雑誌）, 英語

Aspiration Risk Detection Using Oral Administration of Fluorescent Food --- Preliminary Experiments Using Meat Phantoms ---
Takahiro SUZUKI; Ryohei SAITO; Nobuo KITADA; Takuji KOIKE; Shojiro MAKI; Yukihiro MICHIWAKI; Goro NISHIMURA; Haruki NIWA; Yukio YAMADA
2017 IEEE International Conference on Cyborg and Bionic Systems (CBS 2017), IEEE, 1巻, 出版日 2017年10月17日, 査読付
研究論文（国際会議プロシーディングス）, 英語

A luciferin analogue generating near-infrared bioluminescence achieves highly sensitive deep-tissue imaging.
Takahiro Kuchimaru; Satoshi Iwano; Masahiro Kiyama; Shun Mitsumata; Tetsuya Kadonosono; Haruki Niwa; Shojiro Maki; Shinae Kizaka-Kondoh
Nature communications, 7巻, 掲載ページ 11856-11856, 出版日 2016年06月14日, 査読付, 国際誌, In preclinical cancer research, bioluminescence imaging with firefly luciferase and D-luciferin has become a standard to monitor biological processes both in vitro and in vivo. However, the emission maximum (λmax) of bioluminescence produced by D-luciferin is 562 nm where light is not highly penetrable in biological tissues. This emphasizes a need for developing a red-shifted bioluminescence imaging system to improve detection sensitivity of targets in deep tissue. Here we characterize the bioluminescent properties of the newly synthesized luciferin analogue, AkaLumine-HCl. The bioluminescence produced by AkaLumine-HCl in reactions with native firefly luciferase is in the near-infrared wavelength ranges (λmax=677 nm), and yields significantly increased target-detection sensitivity from deep tissues with maximal signals attained at very low concentrations, as compared with D-luciferin and emerging synthetic luciferin CycLuc1. These characteristics offer a more sensitive and accurate method for non-invasive bioluminescence imaging with native firefly luciferase in various animal models.
研究論文（学術雑誌）, 英語

Synthesis and evaluation of new firefly luciferin analogues for luminescent materials
Ioka, Shuji; Saitoh, Tsuyoshi; Iwano, Satoshi; Suzuki, Koji; Maki, Shojiro; Niwa, Haruki; Miyawaki, Atsushi; Imoto, Masaya; Nishiyama, Shigeru
Chemistry, A European Journal, Chemistry, A European Journal, 22巻, 掲載ページ 1-9, 出版日 2016年, 査読付, ホタル生物発光基質のチアゾリン環（右環部）の硫黄原子を炭素原子に変換した新規化合物の合成と発光活性およびその活性についてまとめた．
研究論文（学術雑誌）, 英語

"Synthesis and evaluation of the luminescent properties of firefly luciferin analogues "
Ioka, Shuji; Saitoh, Tsuyoshi; Iwano, Satoshi; Suzuki, Koji; Maki, Shojiro; Niwa, Haruki; Miyawaki, Atsushi; Imoto, Masaya; Nishiyama, Shigeru
Chemistry, A European Journal, 22巻, 1-9号, 出版日 2016年, 査読付, ホタル生物発光基質のチアゾリン環（右環部）の硫黄原子を炭素原子に変換した新規化合物の合成と発光活性およびその活性についてまとめた．
研究論文（学術雑誌）, 英語

Spectroscopic properties of BF2 complexes of N-(5-phenyl-2- pyrazinyl)pivalamides exhibiting fluorescence in solution and solid state (http://dx.doi.org/10.1016/j.jphotochem.2015.10.014)
Sojiro Hachiya; Daisuke Hashizume; Hiroshi Ikeda; Minoru Yamaji; Shojiro Maki; Haruki Niwa; Takashi Hirano
Journal of Photochemistry and Photobiology A: Chemistry, 331巻, 掲載ページ 206-214, 出版日 2016年, 査読付, Boron difluoride (BF2) complexes of N-(5-phenyl-2-pyrazinyl)pivalamide and its derivatives having a substituent on the phenyl group were prepared and their spectroscopic properties were investigated. It was found that the BF2 complexes show fluorescence in solution and the solid state. The origins of the fluorescence properties are discussed on the basis of the fluorescence yields and lifetimes, crystal structures and DFT calculations. The present work would provide a guide to design BF2 complexes of amidopyrazines exhibiting solid state fluorescence.
研究論文（学術雑誌）, 英語

Multicolor Bioluminescence Obtained Using Firefly Luciferin
Masahiro Kiyama; Ryohei Saito; Satoshi Iwano; Rika Obata; Haruki Niwa; Shojiro A. Maki
CURRENT TOPICS IN MEDICINAL CHEMISTRY, BENTHAM SCIENCE PUBL LTD, 16巻, 24号, 掲載ページ 2648-2655, 出版日 2016年, 査読付, Firefly bioluminescence is widely used in life science research as a useful analysis tool. For example, the adenosine-5'-triphosphate (ATP)-dependent enzymatic firefly bioluminescence reaction has long been utilized as a microbial monitoring tool. Rapid and sensitive firefly luciferin-luciferase combinations are used not only to measure cell viability but also for reporter-gene assays. Recently, bioluminescence was utilized as a noninvasive, real-time imaging tool for living subjects to monitor cells and biological events. However, the number of commercialized luciferase genes is limited and tissue-permeable near-infrared (NIR) region emitting light is required for in vivo imaging. In this review, recent studies describing synthetic luciferin analogues predicted to have red-shifted bioluminescence are summarized. Luciferase substrates emitting red, green, and blue light that were designed and developed in our laboratory are presented. The longest emission wavelength of the synthesized luciferin analogues was recorded at 675 nm, which is within the NIR region. This compound is now commercially available as "Aka Lumine (R)".
研究論文（学術雑誌）, 英語

Fluorescence Properties of Diphenylthiazolo[4,5-b]pyrazines Tuned by Donor-Acceptor Substituent Effects
Tatsuki Nakagawa; Minoru Yamaji; Shojiro Maki; Haruki Niwa; Takashi Hirano
PHOTOCHEMISTRY AND PHOTOBIOLOGY, WILEY-BLACKWELL, 91巻, 4号, 掲載ページ 807-813, 出版日 2015年07月, 査読付, Fluorescence properties of 2,6- and 2,5-diphenylthiazolo[4,5-b]pyrazine (TPy) derivatives having an electron-donating substituent (methoxy and dimethylamino) on the 6- and 5-phenyl groups were studied. It was found that 2,6-diphenyl derivatives fluoresce more efficiently than 2,5-diphenyl derivatives. Furthermore, a 2,6-diphenyl derivative having an additional cyano group on the 2-phenyl ring was an excellent fluorophore showing a wide solvatochromism with great fluorescence yields. Based on the obtained spectroscopic data and mechanistic explanations concerning the substituent effects on the fluorescence properties, useful information on designing new TPy fluorophores is provided.
研究論文（学術雑誌）, 英語

Synthesis and chemiluminescent properties of 6,8-diaryl-2-methylimidazo[1,2-alpha]pyrazin-3(7H)-ones: Systematic investigation of substituent effect at para-position of phenyl group at 8-position
Ryota Saito; Takashi Hirano; Shojiro Maki; Haruki Niwa
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, ELSEVIER SCIENCE SA, 293巻, 掲載ページ 12-25, 出版日 2014年11月, 査読付, 6,8-Diphenylimidazopyrazinone derivatives having a substituent R (R=CF3, H, and OMe) at pare position of the 8-phenyl group were synthesized and their chemiluminescent properties were investigated. The chemiluminescence maxima (CLmax) of these compounds were observed to be in the range of 513-553 nm with a bathochromic shift that increased with the electron-withdrawing character of R, contrary to the previously observed substituent effect at the 6-postion. The chemiluminescence efficiencies (phi(CL)) of these imidazopyrazinones were improved by the introduction of a p-substituted phenyl group at the 8-position. The quantitative investigation of the three quantum efficiencies (phi(R), phi(S), and phi(FL)) whose product gives us phi(CL) revealed that the phi(CL) gains made were largely because of the increase in the values of the fluorescence quantum yields of the corresponding light emitters (phi(FL)). The yields of the singlet-excited emitters (phi(S)) during the chemiluminescent reaction were found to be very small (0.015-0.019), suggesting that one cannot construct an efficient imidazopyrazinone-chemiluminescence system that is comparable to the aequorin bioluminescence system only by using the electronic effects of substituents. (C) 2014 Elsevier B.V. All rights reserved.
研究論文（学術雑誌）, 英語

Substituent effects on fluorescence properties of thiazolo[4,5-b]pyrazine derivatives
Tatsuki Nakagawa; Minoru Yamaji; Shojiro Maki; Haruki Niwa; Takashi Hirano
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, ROYAL SOC CHEMISTRY, 13巻, 12号, 掲載ページ 1765-1772, 出版日 2014年, 査読付, Based on spectroscopic measurements and DFT calculations, fluorescence properties of thiazolo[4,5-b]-pyrazine (TPy) derivatives with the phenyl group at the C2 position were studied. TPys were readily prepared from the corresponding amidopyrazines, which have a similar fluorescent core to a bioluminescence light emitter, Cypridina oxyluciferin. It was found that the introduction of electron-donating (methoxy and dimethylamino) groups onto the 2-phenyl moiety of the TPy derivatives, as well as the phenyl and 4-(dimethylamino) phenyl groups at C2 and C6, respectively, increases the fluorescence yield and appearance of solvatochromic character. The mechanism of increasing the fluorescence yield depending on the substituents is discussed. These findings provide useful information on designing new TPy fluorophores.
研究論文（学術雑誌）, 英語

Synthesis and luminescence properties of biphenyl-type firefly luciferin analogs with a new, near-infrared light-emitting bioluminophore
Chihiro Miura; Masahiro Kiyama; Satoshi Iwano; Kazuto Ito; Rika Obata; Takashi Hirano; Shojiro Maki; Haruki Niwa
TETRAHEDRON, PERGAMON-ELSEVIER SCIENCE LTD, 69巻, 46号, 掲載ページ 9726-9734, 出版日 2013年11月, 査読付, New firefly luciferin analogs of the 4,4 '-substituted biphenyl-type were synthesized. One analog with a 4 '-dimethylamino group possessed bioluminescence activity, emitting near-infrared biological window light at 675 nm suitable for deep-site bioimaging of living animals. The chemiluminescence light-emission maximum of the corresponding methyl ester of the bioluminescence active analog was 500 nm, implying that biphenyl and thiazolinone rings in the light emitter might be placed in a coplanar conformation at the polar luciferase active site. (c) 2013 Elsevier Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

Development of simple firefly luciferin analogs emitting blue, green, red, and near-infrared biological window light
Satoshi Iwano; Rika Obata; Chihiro Miura; Masahiro Kiyama; Kazutoshi Hama; Mitsuhiro Nakamura; Yoshiharu Amano; Satoshi Kojima; Takashi Hirano; Shojiro Maki; Haruki Niwa
Tetrahedron, 69巻, 19号, 掲載ページ 3847-3856, 出版日 2013年05月13日, 査読付, Simple firefly luciferin analogs emitting blue, green, and red light were developed. The longest emission maximum was observed at 675 nm, which belongs to the NIR biological window (650-900 nm), useful for deep site bioimaging of living animals. The analogs showed a slow rise of emission intensity compared with the rapid emission of natural luciferin. The light emission of the adenylated analogs was strongly enhanced compared with those of analogs themselves.© 2013 Elsevier Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

Evaluation of Bioluminescence Activity of Firefly Luciferin Nucleotide Derivatives
Satoshi IWANO; Satoshi KOJIMA; Takashi HIRANO; Shojiro MAKI; Haruki NIWA
ECS Transactions, The Electrochemical society, 50巻, 掲載ページ 1-3, 出版日 2013年, 査読付, 天然ホタル生物発光では，発光酵素はAMP化と酸素化反応の２つの反応に関わっている，AMPの核酸と糖の部位をいくつか変えて，発光活性を測定した．その結果，

糖部位をデオキシリボースに変換すると活性が大きく減衰すること，単環性の核酸でも活性は減衰するが，発光活性さほど失われないことがわかった．
研究論文（学術雑誌）, 英語

5-[4-(Dimethylamino)phenyl]-2-benzamidopyrazines: fluorescent dyes based on Cypridina oxyluciferin
Takashi Hirano; Tatsuki Nakagawa; Ai Kodaka; Shojiro Maki; Haruki Niwa; Minoru Yamaji
RESEARCH ON CHEMICAL INTERMEDIATES, SPRINGER, 39巻, 1号, 掲載ページ 233-245, 出版日 2013年01月, 査読付, To clarify the acyl substitution effect on the fluorescent property of Cypridina oxyluciferin analogs, which have the 4-(dimethylamino)phenyl group at C5, we compared the spectroscopic properties of benzamide 1b and its 2,6-dimethylphenyl derivative 1c in various solvents with those of acetamide 1a. Similarity of the fluorescence wavelengths of 1a-c indicates that the pi-electronic conjugation in the excited singlet (S-1) state is terminated at the acyl group and that the benzamide moiety in 1b has little effect on modulating the florescence color. The similar fluorescence solvatochromism of 1a-c reveals that their S-1 states have a similar intramolecular charge transfer character. The fact that 1a-c have various fluorescence quantum yields and lifetimes depending on solvent polarity and hydrogen bonding interactions in solutions provides information about the decay processes competing with the fluorescence process in the S-1 states. Among 1a-c, benzamide 1b exhibits the most sensitive variation of the fluorescence intensity depending on the solvent used. Similarity of the fluorescence spectra of 1a-c adsorbed in NaY zeolites was also observed, which indicates that the S-1 states of 1a-c give mobile conformers in the NaY supercages. The relationship between the molecular structures of 1a-c and their spectroscopic properties will provide a guide for designing a new fluorophore based on Cypridina oxyluciferin.
研究論文（学術雑誌）, 英語

Anoikis Induction and Inhibition of Peritoneal Metastasis of Pancreatic Cancer Cells by a Nuclear Factor-kappa B Inhibitor, (-)-DHMEQ
Masanori Sato; Kazuaki Nakanishi; Sanae Haga; Masato Fujiyoshi; Motoi Baba; Kazuhiro Mino; Yimin; Haruki Niwa; Hideki Yokoo; Kazuo Umezawa; Yoshihiro Ohmiya; Toshiya Kamiyama; Satoru Todo; Akinobu Taketomi; Michitaka Ozaki
ONCOLOGY RESEARCH, COGNIZANT COMMUNICATION CORP, 21巻, 6号, 掲載ページ 333-343, 出版日 2013年, 査読付, The transcription factor nuclear factor-kappa B (NF-kappa B) plays a crucial role in pancreatic cancer (PC) progression. NF-kappa B is also involved in resistance to anoikis, a special type of apoptosis induced when cells are detached from the extracellular matrix or other cells. Anoikis resistance is related to the metastatic abilities of tumor cells; however, little is known about anoikis induction as it relates to inhibition of PC metastasis by NF-kappa B inhibitors. Here we used a specific NF-kappa B inhibitor, (-)-dehydroxymethylepoxyquinomicin (DHMEQ), to investigate anoikis induction and peritoneal metastasis suppression following NF-kappa B inhibition. We transduced Glue, a secretory form of luciferase, into a PC cell line, AsPC-1 (AsPC-1-Gluc), for our in vivo experiments. (-)-DHMEQ induced anoikis in AsPC-1-Gluc cells as measured by cell survival assays and flow cytometry. The DNA-binding activity of p65 was enhanced immediately after cell detachment from culture dishes in ELISA assays. Some antiapoptotic proteins such as cellular inhibitor of apoptotic protein-1 were consequently upregulated on Western blots. (-)-DHMEQ prevented this increase in p65 activity and the subsequent expressions of antiapoptotic molecules. In a murine xenograft model, anoikis-resistant PC cell lines tended to metastasize to the peritoneum more than anoikis-sensitive cells, suggesting a correlation between anoikis sensitivity and peritoneal metastasis. (-)-DHMEQ successfully inhibited peritoneal metastasis of AsPC-1-Gluc cells. We monitored metastasis inhibition by ex vivo chemiluminescent detection of Glue secreted from tumor cells into murine plasma and by in vivo imaging. Our results suggest that (-)-DHMEQ inhibited peritoneal dissemination by preventing anoikis resistance of PC cells.
研究論文（学術雑誌）, 英語

Spectroscopic studies of the color modulation mechanism of firefly (beetle) bioluminescence with amino-analogs of luciferin and oxyluciferin
Hirano, T; Nagai, H; Matsuhashi, T; Hasumi, Y; Iwano, S; Ito, K; Maki, S; Niwa, H; Viviani, V. R
Photochem. Photobiol. Sci., 11巻, 8号, 掲載ページ 1281-1284, 出版日 2012年08月, 査読付
研究論文（学術雑誌）, 英語

Studies on (-) ESIMS/MS of a glycosaminoglycan disaccharide N-acetyllactosamine-6, 6’-disulfate disodium salt---Charge-localization isomers.
Yoko Ohashi; Masayuki Kubota; Hiroshi Hatase; Takashi Hirano; Shojiro Maki; Haruki Niwa
Int. J. Mass Spectrom., ELSEVIER SCIENCE BV, 312巻, 掲載ページ 179-184, 出版日 2012年02月, 査読付, We previously reported the ESI-MS/MS studies on distinguishing Gal beta 1-4GlcNAc-6,6'-disulfate disodium salt from 2'-epimer,(1) namely Gal beta 1-4ManNAc-6,6'-disulfate [1]. Here, we must emphasize first that distinction of the epimeric pair was successful using either FAB or MALDI, but most effectively done by ESI mass spectrometry. However, though totally independent of our original aim of distinguishing epimers, we later realized that there were some inaccuracies in our assignment of the fragmentation path of negative product ions. Through our intensive studies to establish the right fragmentation path, we now propose a new concept of isomers caused by the difference in the localization of a negative charge in apparently the same MS1 ion of a disaccharide dibasic acid. (C) 2011 Elsevier B.V. All rights reserved.
研究論文（学術雑誌）, 英語

Spectroscopic studies of the color modulation mechanism of firefly (beetle) bioluminescence with amino-analogs of luciferin and oxyluciferin
Takashi Hirano; Hiroyuki Nagai; Takuto Matsuhashi; Yosuke Hasumi; Satoshi Iwano; Kazuto Ito; Shojiro Maki; Haruki Niwa; Vadim R. Viviani
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, ROYAL SOC CHEMISTRY, 11巻, 8号, 掲載ページ 1281-1284, 出版日 2012年, 査読付, Spectroscopic properties of amino-analogs of luciferin and oxyluciferin were investigated to confirm the color modulation mechanism of firefly (beetle) bioluminescence. Fluorescence solvatochromic character of aminooxyluciferin analogs indicates that the bioluminescence of aminoluciferin is useful for evaluating the polarity of a luciferase active site.
研究論文（学術雑誌）, 英語

Bioluminescence characteristics of the fruiting body of Mycena chlorophos
Kenichi Mori; Satoshi Kojima; Shojiro Maki; Takashi Hirano; Haruki Niwa
LUMINESCENCE, WILEY-BLACKWELL, 26巻, 6号, 掲載ページ 604-610, 出版日 2011年11月, 査読付, Bioluminescent fungi are widely distributed on land and most belong to the class Basidomycetes. Light of about 530 nm wavelength maximum is emitted continuously. The molecular basis for the light-emitting process remains unclear. We investigated the characteristics of the bioluminescence using cultivated fruiting bodies of M. chlorophos. Only fresh fruiting bodies exhibited long-lasting light emission; rapid decay of light emission was observed with frozen and freeze-dried samples. Freeze-dried samples can be stored at room temperature under dry conditions and may be useful for the isolation of luciferin. The light emission of the fresh fruiting bodies was maintained in various buffers at varying pH; it could be stopped with pH 4 acetate buffer and could be recovered at pH 6. The isolation of luciferin from the fresh fruiting bodies might be possible by the control of buffer pH. The effect of temperature on the light emission of fruiting bodies indicated that bioluminescence in M. chlorophos may involve enzymatic reaction(s). The solubilization of bioluminescent components from the fruiting bodies could not be achieved with various surfactants. Copyright (C) 2011 John Wiley & Sons, Ltd.
研究論文（学術雑誌）, 英語

Influence of Electron-Donating and Electron-Withdrawing Substituents on the Chemiluminescence Behavior of Coelenterazine Analogs
Saito, R; Hirano, T; Maki, S; Niwa, H; M. Ohashi, M
Bull. Chem. Soc. Jpn., The Chemical Society of Japan, 84巻, 1号, 掲載ページ 90-99, 出版日 2011年01月, 査読付
研究論文（学術雑誌）, 英語

Influence of Electron-Donating and Electron-Withdrawing Substituents on the Chemiluminescence Behavior of Coelenterazine Analogs
Ryota Saito; Takashi Hirano; Shojiro Maki; Haruki Niwa; Mamoru Ohashi
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOC JAPAN, 84巻, 1号, 掲載ページ 90-99, 出版日 2011年01月, 査読付, Coelenterazine analogs 3a-3e possessing various substituents at the para-position of the 6-phenyl group (R = CF3, F, H, OMe, and NMe2) were synthesized, and the chemiluminescent properties of 3a-3e in dimethyl sulfoxide (DMSO) were investigated quantitatively. Chemiluminescence maxima observed in the range of 454-478 nm showed a bathochromic shift as the electron-donating ability of R increased. Chemiluminescence quantum yields (Phi(CL)) were obtained in the range of 0.0006-0.0018. The analog 3a possessing the electron-withdrawing CF3 group showed a slight decrease in its Phi(CL) value. The fluorescence quantum yields (Phi(F)) of the light emitter, 2-acetamidopyrazine anions 4a(-)-4e(-), were observed in the range of 0.005-0.21 and showed substituent dependency in that the increment in the electron-withdrawing ability of R decreases the Phi(F) value. The efficiency of generation of the singlet-excited 4a(-)-4e(-) (Phi(s)) showed a small change in the range of 0.008-0.015. From these quantitative analyses of the quantum efficiencies, we found that an electron-donating substituent R is not required for the efficient generation of a singlet-excited light emitter, but is required for the high Phi(F) of the emitter.
研究論文（学術雑誌）, 英語

Colorimetric and fluorometric sensing of the Lewis acidity of a metal ion by metal-ion complexation of imidazo[1,2-a]pyrazin-3(7H)-ones
Takashi Hirano; Takashi Sekiguchi; Daisuke Hashizume; Hiroshi Ikeda; Shojiro Maki; Haruki Niwa
TETRAHEDRON, PERGAMON-ELSEVIER SCIENCE LTD, 66巻, 21号, 掲載ページ 3842-3848, 出版日 2010年05月, 査読付, Metal-ion complexation of 7-benzylimidazo[1,2-a]pyrazin-3(7H)-one derivative (2) with Li+, Mg2+, Ca2+, Ba2+, Sc3+, and La3+ in acetonitrile resulted in successive modulations of its UV/vis absorption and fluorescence spectroscopic properties. This result indicates that 2 can be used as a calorimetric and fluorometric sensor of the Lewis acidity of a metal ion in aprotic solutions. The hypothesis that the metal-ion complex has a O10(imidazopyrazinone)-metal ion bond was supported by X-ray crystallographic analysis and quantum chemical calculations for a Li+ complex of 7-methylimidazo[1,2-a]pyrazin-3(7H)-one derivative (1). (C) 2010 Elsevier Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

Synthesis and properties of bis(pyrazino[2 ',3 ':4,5]imidazole)-fused 1,2,5,6-tetrahydro-1,4,5,8,9,10-hexaazaanthracenes: a new fluorescent nitrogen-rich heterocycle
Sojiro Hachiya; Daisuke Hashizume; Shojiro Maki; Haruki Niwa; Takashi Hirano
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 51巻, 10号, 掲載ページ 1401-1403, 出版日 2010年03月, 査読付, Nitrogen-rich heterocycles, bis(pyrazino[2',3':4,5]imidazole)-fused 1,2,5,6-tetrahydro-1,4,5,8,9,10-hexaazaanthracenes (BPI-HAAs) were prepared by conventional Pd(OAc)(2)/BINAP-catalyzed C-N coupling reactions of 5-aryl-3-bromoaminopyrazines. The BPI-HAA core is a planar structure with aromaticity, and this heterocycle exhibits red fluorescence and moderate electron-accepting characteristics. (C) 2010 Elsevier Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

Synthesis and fluorescence properties of difluoro[amidopyrazinato-O,N]boron derivatives: a new boron-containing fluorophore
Sojiro Hachiya; Takayuki Inagaki; Daisuke Hashizume; Shojiro Maki; Haruki Niwa; Takashi Hirano
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 51巻, 12号, 掲載ページ 1613-1615, 出版日 2010年03月, 査読付, New boron-containing fluorophores, difluoro[amidopyrazinato-O,N]boron (APB) derivatives, were prepared from amidopyrazines. The fluorescence properties of APB were successfully modulated by an aryl substitution at the C8 position. (C) 2010 Elsevier Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

Distinction of Sialyl Anomers on ESI- and FAB-MS/MS: Stereo-Specific Fragmentations
Yoko Ohashi; Masayuki Kubota; Hiroshi Hatase; Mitsuhiro Nakamura; Takashi Hirano; Haruki Niwa; Yoshitaka Nagai
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, ELSEVIER SCIENCE INC, 20巻, 3号, 掲載ページ 394-397, 出版日 2009年03月, 査読付, An anomeric pair of the lysoglyceroganglioside 1-O-octadecyl-3-O-(N-acetyl)neuraminyl-sn-glycerol sodium salt was studied to see if sialic anomers were distinguishable by mass spectra. It was evident that, in the electrospray ionization and fast-atom bombardment product-ion spectra: (1) in the positive MS(2) product-ion spectrum, the beta- anomer showed an unexpected aglycone-side sodiated sodium alkoxide ion, which was absent for the a-anomer; (2) in both polarities the beta-anomer showed dehydration much more easily than the a-anomer; and (3) in the negative MS(2) product-ion spectrum, the P-anomer also readily showed decarboxylation. Our hypothesis is that, although several easily interconvertible conformations may be allowed, the one having the large aglycone in the equatorial orientation affects the collision-induced dissociation fragmentations. (J Am Soc Mass Spectrom 2009, 20, 394-397) (C) 2009 Published by Elsevier Inc. on behalf of American Society for Mass Spectrometry
研究論文（学術雑誌）, 英語

Spectroscopic Studies of the Light-Color Modulation Mechanism of Firefly (Beetle) Bioluminescence
Takashi Hirano; Yosuke Hasumi; Kazuhiro Ohtsuka; Shojiro Maki; Haruki Niwa; Minoru Yamaji; Daisuke Hashizume
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMER CHEMICAL SOC, 131巻, 6号, 掲載ページ 2385-2396, 出版日 2009年02月, 査読付, To reveal the light-color modulation mechanism of firefly (beetle) bioluminescence, we investigated the spectroscopic properties of the phenolate anion 1-O- generated from 5,5-dimethyloxyluciferin (1-OH) using various base/solvent combinations. Phenolate anion 1-O- is a model compound for the keto form of wild-type oxyluciferin phenolate anion (OL-), which is postulated to be the emitter of the bioluminescence. The fluorescence maxima of 1-O- were found to depend on the base/solvent combination used, and they varied in the range 541-640 nm, which covers the almost whole range of the bioluminescence emission maximum. In a polar solvent, where (1)(1-O-)* and the countercation (the conjugate acid of a base) make a solvent-separated ion pair or a free ion couple, the emission maxima of 1-O- were found to be modulated by the solvent polarity. In a less polar solvent, where (1)(1-O-)* and the countercation are formed as a contact ion pair, the strength of the covalent character of the O8'center dot center dot center dot H bond between (1)(1-O-)* and the countercation is operative. The effect of the base/solvent combination on the emission properties of (1)(1-O-)* was also verified using fluorescence lifetime measurements and density functional theory calculations on 1-O- and its ion-pair models. On the basis of these results, we propose the following light-color modulation mechanism: (1) the light emitter is the excited singlet state of OL- [ (1)(OL-)*], and (2) light emission from (1)(OL-)* is modulated by the polarity of the active-site environment of a luciferase and the degree of covalent character of the O8'center dot center dot center dot H bond between (1)(OL-)* and a protonated basic moiety in the active site. Mechanisms for variation of the bioluminescence colors and their applications are discussed.
研究論文（学術雑誌）, 英語

CHEMIEXCITATION MECHANISM FOR CYPRIDINA (VARGULA) AND AEQUOREA BIOLUMINESCENCE
T. Hirano; H. Ohba; Y. Takahashi; S. Maki; S. Kojima; H. Ikeda; H. Niwa
BIOLUMINESCENCE AND CHEMILUMINESCENCE, WORLD SCIENTIFIC PUBL CO PTE LTD, 掲載ページ 19-22, 出版日 2009年, 査読付
研究論文（国際会議プロシーディングス）, 英語

The reaction mechanism for the high quantum yield of Cypridina (Vargula) bioluminescence supported by the chemiluminescence of 6-aryl-2-methylimidazo[1,2-a]pyrazin-3(7H)-ones (Cypridina luciferin analogues)
Takashi Hirano; Yuto Takahashi; Hiroyuki Kondo; Shojiro Maki; Satoshi Kojima; Hiroshi Ikeda; Haruki Niwa
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, ROYAL SOC CHEMISTRY, 7巻, 2号, 掲載ページ 197-207, 出版日 2008年, 査読付, To establish the reaction mechanism of the high-quantum-yield bioluminescence in Cypridina (Vargula), we investigated the chemiluminescence of 6-aryl-2-methylimidazo[1,2-a] pyrazin-3(7H)-ones (1H) as Cypridina luciferin analogues in DMSO-1,1,3,3-tetramethylguanidine and in diglyme-acetate buffer. We found that the chemiluminescence of 1H with an electron-donating aryl group, such as a 4-(dimethylamino) phenyl, 3-indolyl or 3-(1-methyl) indolyl group, gave a high quantum yield (Phi(CL)) in diglymeacetate buffer. This indicates that the reaction mechanism producing this high Phi(CL) involves the chemiexcitation of a neutral dioxetanone intermediate possessing an electron-donating aryl group to the singlet excited state of neutral acetamidopyrazine (the light emitter). In addition, we investigated the. fluorescence of acetamidopyrazines and performed DFT calculations for neutral dioxetanones and the transition states (TS) of the dioxetanone's decomposition. The results made it clear that the electron-donating aryl group gives the TS and the singlet-excited acetamidopyrazine (S-1) a strong intramolecular charge transfer (ICT) character, and their similar ICT character leads to the ICT TS -> S-1 route in the charge transfer-induced luminescence (CTIL) mechanism for efficient chemiexcitation. The reaction mechanism of the chemiluminescence of 1H can explain the highly efficient chemiexcitation of Cypridina bioluminescence.
研究論文（学術雑誌）, 英語

Electrolysis and its hybrid methods applied to decomposition of endocrine disrupting chemicals
Naomi Takagami; Kazuhiro Ohtsuki; Shojiro Maki; Haruki Niwa; Shin-ichi Hatanaka; Shigeo Hayashi
ELECTROCHEMISTRY, ELECTROCHEMICAL SOC JAPAN, 74巻, 8号, 掲載ページ 599-602, 出版日 2006年08月, 査読付, Rate constants for decomposition reaction were measured for several phenols, i.e., bisphenol A, p-chlorophenol, p-octylphenol, 2,4-dichlorophenol, p-tert-butylphenol and for two other chemicals, benzophenone and PCB compounds in waste oil. The following methods were adopted: electrolysis, photolysis, sonolysis, photolytic electrolysis, and sonolytic electrolysis. The initial concentration was fixed at 50 mg/L except for the PCB, for which the concentration for all the isomers was 500 ng/L. The solvent was water, but for chemicals with insufficient solubility, mixtures with alcohols were used. Additional application of ultrasound led to remarkable enhancement for p-chlorophenol and 2,4-dichlorophenol. The electrolysis rate constant for PCB compounds was comparable to that for the phenols. Benzophenone was decomposed 10 times as slow as the phenols partly because of the solvent containing alcohols.
研究論文（学術雑誌）, 英語

Chemiluminescence of 6-aryl-2-methylimidazo[1,2-a]pyrazin-3(7H)-ones in DMSO/TMG and in diglyme/acetate buffer: support for the chemiexcitation process to generate the singlet-excited state of neutral oxyluciferin in a high quantum yield in the Cypridina (Vargula) bioluminescence mechanism
Yuto Takahashi; Hiroyuki Kondo; Shojiro Maki; Haruki Niwa; Hiroshi Ikeda; Takashi Hirano
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 47巻, 34号, 掲載ページ 6057-6061, 出版日 2006年08月, 査読付, The chemiluminescence of 6-aryl-2-methylimidazo [1,2-a]pyrazin-3 (7 H) -ones (Cypridina luciferin analogues) in DMSO/ 1,1,3,3-tetramethylguanidine and in diglyme/acetate buffer was investigated. The results indicate that the reaction mechanism that produces a high chemiluminescence quantum yield involves a chemiexcitation process from a neutral dioxetanone intermediate possessing an electron-donating aryl group (sigma(Ar) <-0.6) to the singlet-excited state of neutral acetamidopyrazine. This result may be applied to the reaction mechanism for Cypridina (Vargula) bioluminescence. (c) 2006 Elsevier Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

Real light emitter in the bioluminescence of the calcium-activated photoproteins aequorin and obelin: light emission from the singlet-excited state of coelenteramide phenolate anion in a contact ion pair
Kotaro Mori; Shojiro Maki; Haruki Niwa; Hiroshi Ikeda; Takashi Hirano
TETRAHEDRON, PERGAMON-ELSEVIER SCIENCE LTD, 62巻, 26号, 掲載ページ 6272-6288, 出版日 2006年06月, 査読付, Fluorescence of the phenolate anion (3(O)(-)) and the amide anion (5(N)(-)) of coelenteramide analogues in ion pairs with various counter cations was systematically investigated to elucidate the ionic structure of the light emitter in the bioluminescence of the calcium-activated photoproteins aequorin and obelin. The fluorescent properties of 3(O)- in an ion pair with a conjugate acid of an organic base (BASE-H+) were varied depending on the structural variation of the ion pair and the solvent polarity. In particular, the fluorescence of 3(O)- in the ion pair with the conjugate acid of n-butylamine (NBA-H+) indicates that the singlet-excited state of 3(O)(-) ((1)3(O)(-)*) and NBA-H+ make a contact ion pair in which the fluorescence emission maxima of 3(O)- is sensitive to the solvent polarity and the fluorescence quantum yields of 3(O)- increase in a less polar solvent. The results also confirm that (1)3(O)-* is a twisted intramolecular charge transfer state. By contrast, the fluorescence of 5(N)(-) in an ion pair depends little on the BASE-H+ or the solvent polarity. Based on these results, we conclude that the light emitter in aequorin and obelin bioluminescences is the singlet-excited state of coelenteramide phenolate anion 2(O)(-)((1)2(O)(-)*) in a contact ion pair with an imidazolium side chain of a histidine residue, which is located at the less polar active sites of the photoproteins. We also propose a mechanism for the bioluminescence reaction, including the chemiexcitation process to give (1)2(O)(-)*. (c) 2006 Elsevier Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

Construction of a New Firefly Bioluminescence System using L-luciferin
Mitsuhiro Nakamura; Kazuki Niwa; Shojiro Maki; Takashi Hirano; Yoshihiro Ohmiya; Haruki Niwa
Tetrahedron Letters, 47巻, 7号, 掲載ページ pp. 1197-1200, 出版日 2006年, 査読付
研究論文（学術雑誌）, 英語

Substituent effects on the kinetics for the chemiluminescence reaction of 6-arylimidazo[1,2-a]pyrazin-3(7H)-ones (Cypridina luciferin analogues): support for the single electron transfer (SET)–oxygenation mechanism with triplet molecular oxyg
Hiroyuki Kondo; Takayuki Igarashi; Shojiro Maki; Haruki Niwa; Hiroshi Ikeda; Takashi Hirano
Tetrahedron Letters, PERGAMON-ELSEVIER SCIENCE LTD, 46巻, 45号, 掲載ページ 7701-7704, 出版日 2005年11月, 査読付, Kinetics of chemiluminescence reactions of 2-methyl-6-phenylimidazo[1,2-a]pyrazin-3 (7H)-one (1c, Cypridina luciferin analogue) and substituent effects of the 6-aryl group of derivatives 1 strongly suggest that the rate-determining step is a single electron transfer from an anion derived from 1 to a triplet molecular oxygen (O-2) in the oxygenation process. (c) 2005 Elsevier Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

Substituent effects on the spectroscopic properties of solvatochromic 2-phenylimidazo[1,2-a]pyrazin-3(7H)-ones: an effective control for the colorimetric sensor properties
Y Takamuki; S Maki; H Niwa; H Ikeda; T Hirano
TETRAHEDRON, PERGAMON-ELSEVIER SCIENCE LTD, 61巻, 42号, 掲載ページ 10073-10080, 出版日 2005年10月, 査読付, Substituent effects on the spectroscopic properties of a solvatochromic compound, 7-methyl-2-phenylimidazo[1,2-a]pyrazin-3(7H)-one (1c), using derivatives 1 with a para-substituent R on the phenyl group, were investigated systematically. In the UV/visible absorption spectra, the solvatochromic property of I originating from hydrogen-bonding interactions was effectively regulated by the substituent effects. In particular, the cyano derivative le showed significant solvatochromism with a wide color variation range and a high sensitivity toward solvents. Similarly, the fluorescence of I showed a redshift as the electron-withdrawing property of R increased. The substituent effects were evaluated by AM1-COSMO calculations, which also suggested that derivatives 1 are good electron donors and that the electron-donating ability is regulated by R. This was confirmed by the observation of low oxidation potentials and the formation of charge-transfer complexes with tetracyanoethylene. Absorption-spectrum changes of le and le caused by metal-ion complexation were also compared, showing that the cyano derivative le is a good colorimetric sensor for the Lewis acidity of the metal ions. From these observations, it was established that para-substitution of R on the phenyl group of le caused successive modulations of the colorimetric sensor properties. (c) 2005 Elsevier Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

Bioluminescence in the limpet-like snail Latia neritoides.
Yoshihiro Ohmiya; Satoshi Kojima; Mitsuhiro Nakamura; Haruki Niwa
Bull. Chem. Soc. Jpn., 78巻, 7号, 掲載ページ pp. 1197-1205, 出版日 2005年07月, 査読付
研究論文（学術雑誌）, 英語

Firefly luciferase exhibits bimodal action depending on the luciferin chirality
M Nakamura; S Maki; Y Amano; Y Ohkita; K Niwa; T Hirano; Y Ohmiya; H Niwa
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, ACADEMIC PRESS INC ELSEVIER SCIENCE, 331巻, 2号, 掲載ページ 471-475, 出版日 2005年06月, 査読付, Firefly luciferase is able to convert (L)-luciferin into luciferyl-CoA even under ordinary aerobic luciferin-luciferase reaction conditions. The luciferase is able to recognize strictly the chirality of the luciferin structure, serving as the acyl-CoA synthetase for (L)-luciferin, whereas (D)-luciferin is used for the bioluminescence reaction. (D)-Luciferin inhibits the luciferyl-CoA synthetase activity Of (L)-luciferin, whereas (L)-luciferin retards the bioluminescence reaction Of (D)-luciferin, meaning that both enzyme activities are prevented by the enantiomer of its own substrate. © 2005 Elsevier Inc. All rights reserved.
研究論文（学術雑誌）, 英語

Electron-transfer oxygenation mechanism in the chemiluminescence reaction of imidazo[1,2-a]pyrazin-3(7H)-one with triplet dioxygen
Hiroyuki Kondo; Takayuki Igarashi; Shojiro Maki; Haruki Niwa; Hiroshi Ikeda; Takashi Hirano
Tetrahedron Letters, 46巻, 掲載ページ 7701-7704, 出版日 2005年, 査読付, ウミホタル生物発光反応を確立するため，６位のフェニル基上に種々置換基を導入した誘導体を用いて，詳細な化学発光反応の速度論を解析した．この結果，反応機構中，酸素化過程が電子移動によって支配されていることを明らかにした．
研究論文（学術雑誌）, 英語

Characterization of [1-13C]-Specifically Labeled Amino Acids Using ESIMS/MS in the Selected Reaction Monitoring Mode
Yoko Ohashi; Hiroshi Hatase; Mitsuhiro Nakamura; Takashi Hirano; Shojiro Maki; Haruki Niwa
Journal of the Mass Spectrometry Society of Japan, the Mass Spectrometry Society of Japan, 53巻, 掲載ページ 309-314, 出版日 2005年, 査読付
研究論文（学術雑誌）, 英語

6,8-diarylimbazo[1, 2-a]pyrazin-3(7H) - Ones as potential chemiluminescent pH/superoxide double sensors
R Saito; N Suga; A Katoh; S Maki; T Hirano; H Niwa
Bioluminescence & Chemiluminescence: Progress and Perspectives, WORLD SCIENTIFIC PUBL CO PTE LTD, 掲載ページ 335-338, 出版日 2005年, 査読付
研究論文（国際会議プロシーディングス）, 英語

Development of the chemistry of the imidazopyrazionone-bioluminescence system: From the bio- and chemiluminescence mechanism to a design of sensor molecules
T Hirano; S Nakai; S Sekiguchi; S Fujio; S Maki; H Niwa
Bioluminescence & Chemiluminescence: Progress and Perspectives, WORLD SCIENTIFIC PUBL CO PTE LTD, 掲載ページ 117-120, 出版日 2005年, 査読付
研究論文（国際会議プロシーディングス）, 英語

Bioluminescence activity of Latia luciferin analogues: replacement of the 2,6,6-trimethylcyclohexene ring onto the methyl-substituted phenyl groups
M Nakamura; M Mamino; M Masaki; S Maki; R Matsui; S Kojima; T Hirano; Y Ohmiya; H Niwa
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 46巻, 1号, 掲載ページ 53-56, 出版日 2005年01月, 査読付, A series of Latia luciferin analogues having methyl-substituted phenyl groups instead of the natural 2.6.6-trimethylhexene ring was synthesized and their bioluminescence activity were measured. The Latia luciferase was found to be able to moderately recognize the appropriately methyl-substituted phenyl analogues with the same light production kinetics as. that of natural luciferin. (C) 2004 Elsevier Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

Characterization of Regio-specific 13CO-Labeling of Amino Acids Using ESIMS/MS in the SRM Mode.
Yoko OHASHI; Hiroshi HATASE; Mitsuhiro NAKAMURA; Takashi HIRANO; Shojiro MAKI; Haruki NIWA
J. Mass Spectrom. Soc. jpn, 53巻, 6号, 掲載ページ pp. 309-314, 出版日 2005年, 査読付
研究論文（学術雑誌）, 英語

Substituent effects on the solvatochromism of 2-phenylimidazopyrazinones: Effective control of the color variation range and sensitivity toward an indication of the proton-donor ability of solvents by an electron-withdrawing group substitution
Y Takamuki; S Maki; H Niwa; H Ikeda; T Hirano
CHEMISTRY LETTERS, CHEMICAL SOC JAPAN, 33巻, 11号, 掲載ページ 1484-1485, 出版日 2004年11月, 査読付, A para-substitution on the phenyl group of 2-phenylimida-zopyrazinone successively resulted in a change of the solvato-chromic property, especially of the color-variation range and sensitivity to solvents, demonstrating that derivatives possessing an electron-withdrawing group are preferable as potential indicators of the proton-donor ability of solvents.
研究論文（学術雑誌）, 英語

Regioselective phenyl-substitution effects on the solvatochromism of 2-phenylimidazo[1,2-a]pyrazin-3(7H)-one derivatives: Expansion of the color variation range of a visible indicator for the proton donor ability of solvents.
Shunsuke Fujio; Daisuke Hashizume; Yoshiharu Takamuki; Masanori Yasui; Fujiko Iwasaki; Shojiro Maki; Haruki Niwa; Hiroshi Ikeda; Takashi Hirano
Tetrahedron Letters, 45巻, 46号, 掲載ページ pp. 8531-8534, 出版日 2004年10月, 査読付
研究論文（学術雑誌）, 英語

Synthesis of prostaglandin F ethanolamide by prostaglandin F synthase and identification of Bimatoprost as a potent inhibitor of the enzyme: new enzyme assay method using LC/ESI/MS
N Koda; Y Tsutsui; H Niwa; S Ito; DF Woodward; K Watanabe
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, ELSEVIER SCIENCE INC, 424巻, 2号, 掲載ページ 128-136, 出版日 2004年04月, 査読付, Prostaglandin (PG) D-2 ethanolamide (prostamide D-2) was reduced to 9alpha, 11beta-PGF(2) ethanolamide (9alpha, 11beta-prostamide F-2) by PGF synthase, which also catalyzes the reduction of PGH(2) and PGD(2) to PGF(2alpha) and 9alpha11beta-PGF(2), respectively. These enzyme activities were measured by a new method, the liquid chromatographic-electrospray ionization-mass spectrometry (LC/ESI/MS) technique, which could simultaneously detect the substrate and all products. PGF(2alpha), 9alpha,l lbeta-PGF(2), PGD(2), PGH(2), 9alpha,11beta-prostamide F-2, and prostamide D-2 were separated on a TSKgel ODS 80Ts column, ionized by electrospray, and detected in the negative mode. Selected ion monitoring (SIM) of m/z 353 ([M-H](-)), 353 ([M-H](-)), 351 ([M-H](-)) 333 ([M-H-H2O](-)) 456 ([M+59](-)), and m/z 358 ([M-37](-)) was used for quantifying PGF(2alpha), 9alpha,11beta-PGF(2), PGD(2), PGH(2), 9alpha,11beta-prostamide F-2, and prostamide D-2, respectively. The detection limit for PGF(2alpha) and 9alpha,11beta-PGF(2) was 0.01 pmol, that for PGH(2) and PGD(2), 0.1 pmol; and that for prostamide D-2 and 9alpha,11beta-prostamide F-2, 0.5 and 0.03 pmol, respectively. The LC/ESI/MS technique for measuring PGF synthase activity showed higher sensitivity than other methods. Using this method, we found that Bimatoprost, the ethyl amide analog of 17-phenyl-trinor PGF(2alpha) and an anti-glaucoma agent, inhibited all three reductase activities of PGF synthase when used at a low concentration. These results suggest that Bimatoprost also behaves as a potent PGF synthase inhibitor in addition to having prostamide-like activity. (C) 2004 Elsevier Inc. All rights reserved.
研究論文（学術雑誌）, 英語

Synthesis of Latia Luciferin Benzoate Analogues and those Bioluminescent Activity.
Mitsuhiro Nakamura; Mizuki Masaki; Shojiro Maki; Ryo Matsui; Minako Hieda; Masashi Mamino; Takashi Hirano; Yoshihiro Ohmiya; Haruki Niwa
Tetrahedron Letters, 45巻, 10号, 掲載ページ pp. 2203-2205, 出版日 2004年02月, 査読付
研究論文（学術雑誌）, 英語

Analysis of sugar epimers using mass spectrometry: N-acetyllactosamine-6,6 '-disulfate and the 2 '-epimer
Y Ohashi; Y Itoh; M Kubota; K Hamada; M Ohashi; T Hirano; H Niwa
EUROPEAN JOURNAL OF MASS SPECTROMETRY, IM PUBLICATIONS, 10巻, 2号, 掲載ページ 269-278, 出版日 2004年, 査読付, Galbeta1-4GlcNAc-6,6'-disulfate and 2'-epimer corresponding to Galbeta1-4ManNAc-6,6'-disulfate were distinguished by mass spectrometry by utilizing fast atom bombardment (FAB), electrospray ionization (ESI) and matrix-assisted laser desorption/ionization (MALDI) methods. As for the steric information, negative-ion ESI mass spectrometry/mass spectrometry (MS/MS) provides the most extensive data, but FAB MS/MS also reveals detailed structural information of interest in our case, where MALDI MS is not yet fully equipped with post-source decay.
研究論文（学術雑誌）, 英語

Metal-ion complexation of imidazo[1,2-a]pyrazin-3(7H)-ones: continuous changes in absorption spectra of complexes depending on the Lewis acidity of the metal ion
T Sekiguchi; S Maki; H Niwa; H Ikeda; T Hirano
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 45巻, 5号, 掲載ページ 1065-1069, 出版日 2004年01月, 査読付, The spectroscopic properties of metal-ion complexes of several imidazopyrazinone derivatives with Li+, Mg2+, Ca2+, Ba2+, Sc3+, and La3+ ions were studied. The spectral characteristics and the formation constants of the complexes changed continuously depending on the Lewis acidity of the metal ion, suggesting that the imidazopyrazinones can find application as indicators of Lewis acidity. In the case of bis-imidazopyrazinone derivatives, the complexation abilities were enhanced by chelate effects. (C) 2003 Elsevier Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

Fundamental studies on the structures and spectroscopic properties of imidazo[1,2-a]pyrazin-3(7H)-one derivatives
S Nakai; M Yasui; M Nakazato; F Iwasaki; S Maki; H Niwa; M Ohashi; T Hirano
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOC JAPAN, 76巻, 12号, 掲載ページ 2361-2387, 出版日 2003年12月, 査読付, The fundamental physical properties of 2-methyl and 2-phenylimidazo[1,2-a]pyrazin-3(7H)-one 1 and 2, and their N- and O-alkylated derivatives 3-6 have been investigated by X-ray crystallography, UV/vis absorption spectroscopy, NMR, and AMl-COSMO calculations. The crystal structures of 3 and 4 showed that the imidazo[1,2-a]pyrazin-3(7H)-one (imidazopyrazinone) pi-system has a planar ring structure and a weakened carbonyl character of the C3-O10 bond, suggesting that the imidazopyrazinone pi-system has the character of a zwitter-ionic resonance structure to increase the aromaticity. The data concerning the bond length alternations and the NMR chemical shifts of 1-4 also support that their imidazopyrazinone rings have small portions of aromatic character. In addition, imidazopyrazinone derivatives 1-4 showed solvatochromism originating by hydrogen-bonding interactions with hydrogen-bond donor solvent molecules; derivatives 1 and 2 prefer to be the NH form isomers in their tautomeric equilibriums. These observations were consistently evaluated by MO calculations. The physical properties of protonated species of 1-6 and anion species of 1 and 2 were also established. The fundamental properties of the imidazopyrazinone pi-system explain the several problems of the chemi- and bioluminescence reactivities of imidazopyrazi none derivatives and of the construction of a bioluminescent supramolecule.
研究論文（学術雑誌）, 英語

Essential (110)Cys in active site of membrane-associated prostaglandin E synthase-2
K Watanabe; H Ohkubo; H Niwa; N Tanikawa; N Koda; S Ito; Y Ohmiya
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, ACADEMIC PRESS INC ELSEVIER SCIENCE, 306巻, 2号, 掲載ページ 577-581, 出版日 2003年06月, 査読付, The amino acid sequence of membrane-associated prostaglandin (PG) E synthase-2 (mPGE synthase-2), which has a broad specificity in its thiol requirement for a catalytic activity, has the consensus region from (104)Leu to (120)Leu found in glutaredoxin and of thioredoxin. The sequence of Cys-x-x-Cys in the consensus region is the active site for thioredoxin and mPGE synthase-2 also has this amino acid sequence ((110)Cys-x-x-(113)Cys). The mutation from (110)Cys to Ser or the double mutation from (110)Cys and (113)Cys to Ser caused loss of PGE synthase activity, whereas the single mutation from (110)Cys to Ser did not affect the enzyme activity. These results indicate that (110)Cys, but not (113)Cys, is the essential amino acid in the active site of mPGE synthase-2. (110)Cys is an important amino acid in PGE synthase activity and plays the critical role as Cys at the same position in redoxin. Moreover, we found that the reduced form of lipoic acid (dihydrolipoic acid) serves as one of the natural activators of mPGE synthase-2 in the cells. (C) 2003 Elsevier Science (USA). All rights reserved.
研究論文（学術雑誌）, 英語

Pd black deposited on polypropylene sheet as a highly selective catalyst for hydrogenation of alkenes
S Maki; M Okawa; T Makii; T Hirano; H Niwa
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 44巻, 18号, 掲載ページ 3717-3721, 出版日 2003年04月, 査読付, A catalyst deposited on a polypropylene sheet having an activity of almost the same level as commercially available Pd black and capable of promoting hydrogenolysis-free hydrogenation was developed. (C) 2003 Elsevier Science Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

Hydrogenolysis-free Hydrogenation Using Pd Black Catalyst Deposited on Pd Sheet.
Shojiro Maki; Makiko Okawa; Toshimichi Makii; Takashi Hirano; Haruki Niwa
ITE Letters on Batteries, New Technologies and Medicine, 4巻, 1号, 掲載ページ pp. 49-54, 出版日 2003年, 査読付
研究論文（学術雑誌）, 英語

Viscosity-dependent fluorescence decay of the GFP chromophore in solution due to fast internal conversion
AD Kummer; C Kompa; H Niwa; T Hirano; S Kojima; ME Michel-Beyerle
JOURNAL OF PHYSICAL CHEMISTRY B, AMER CHEMICAL SOC, 106巻, 30号, 掲載ページ 7554-7559, 出版日 2002年08月, 査読付, Time-resolved fluorescence measurements at 275 K show that the excited-state lifetime of a model chromophore of the green fluorescent protein (GFP) substantially increases from subpicoseconds in low-viscosity solvents such as ethanol (eta = 1.7 cP) to 30 ps in glycerol (eta = 9.9 x 10(3) cP) and reaches 2.1 ns in glycerol glass at 150 K. At high temperatures the similarity of excited-state decay and ground-state recovery kinetics indicates internal conversion being responsible for the short fluorescence lifetimes. Their viscosity dependence reflects on a motion with a considerable amplitude that is damped by viscous drag and outweighs thermal activation as is concluded from measurements at different temperatures. In solution the neutral and the anionic forms of the model chromophore are similarly nonfluorescent in contrast to wild-type GFP and mutants where the deprotonated form is hardly undergoing internal conversion. Thus, the protein selectively restricts motional degrees of freedom of the chromophore in specific protonation states.
研究論文（学術雑誌）, 英語

Preparation of Deoxygenated Derivatives of Neoanisatin, a Neurotoxic Sesquiterpenoid Having a β-Lactone.
Kazuyoshi Obitsu; Shojiro Maki; Takashi Hirano; Haruki Niwa
Bull. Chem. Soc. Jpn., CHEMICAL SOC JAPAN, 75巻, 2号, 掲載ページ 347-354, 出版日 2002年02月, 査読付, Seven deoxygenated neoanisatin derivatives were prepared from anisatin and neoanisatin by utilizing methoxalyl ester/tributylstannane (n-Bu3SnH) deoxygenation procedure coupled with a novel dehydration reaction of neoanisatin.
研究論文（学術雑誌）, 英語

Reduction in Desorption Mass Spectrometry: Multiple Protonation on Flavins without Charge Increment.
Yoshiyuki Itoh; Yoko Ohashi; Toshimichi Shibue; Akio Hayashi; Shojiro Maki; Takashi Hirano; Haruki Niwa
J. Mass Spectrom. Jpn., 50巻, 2号, 掲載ページ pp. 52-57, 出版日 2002年, 査読付
研究論文（学術雑誌）, 英語

Preparation and Toxic Property of Carbapicrotoxinin, a Cyclopropane-containing Analog of a GABA-antagonistic Sesquiterpenoid Picrotoxinin.
Kazuyoshi Obitsu; Shojiro Maki; Takashi Hirano; Haruki Niwa
ITE Letters on Batteries, New Technologies and Medicine, 3巻, 3号, 掲載ページ pp. 358-361, 出版日 2002年, 査読付
研究論文（学術雑誌）, 英語

Fluorescence properties of phenolate anions of coelenteramide analogues: the light-emitter structure in aequorin bioluminescence
Y Imai; T Shibata; S Maki; H Niwa; M Ohashi; T Hirano
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, ELSEVIER SCIENCE SA, 146巻, 1-2号, 掲載ページ 95-107, 出版日 2001年12月, 査読付, To elucidate the ionic structure of the excited state of light-emitter coelenteramide in aequorin bioluminescence, the fluorescent properties of phenolate anions of coelenteramide analogues were investigated. Fluorescence of phenolate anion in non-polar solvents was observed by electronic excitation of a 1: 1 hydrogen-bonded complex of a coelenteramide analogue with a hydrogen-bond donor molecule such as n-butylamine. In polar solvents, the phenolate anion was directly generated using a base, and its fluorescence was studied. These results confirm that the singlet-excited state of phenolate anion of coelenteramide has an intramolecular CT character, and that its fluorescence emission wavelength changes depending upon solvent polarity. The fluoro-substituent effect on the fluorescent property of phenolate anions was also clarified to help in explaining the bioluminescent property of fluorinated semi-synthetic aequorin. These results consistently support the assignment that the phenolate anion is the ionic structure of the excited light-emitter in BFP during AQ bioluminescence. (C) 2001 Elsevier Science B.V. All rights reserved.
研究論文（学術雑誌）, 英語

Effect of solvent and hydrogen during selective hydrogenation
S Maki; Y Harada; R Matsui; M Okawa; T Hirano; H Niwa; M Koizumi; Y Nishiki; T Furuta; H Inoue; C Iwakura
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 42巻, 47号, 掲載ページ 8323-8327, 出版日 2001年11月, 査読付, Described is the solvent effect for the chemoselective hydrogenation of alkenes having a benzyloxy group (Bn-O-) using a hydrogenation system employing atomic hydrogen permeating through a Pd sheet electrode. (C) 2001 Elsevier Science Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

Hydrogenolysis-free hydrogenation by Pd black powder catalyst
S Maki; M Okawa; R Matsui; T Hirano; H Niwa
SYNLETT, GEORG THIEME VERLAG KG, 10号, 掲載ページ 1590-1592, 出版日 2001年10月, 査読付, A new general method of hydrogenolysis-free hydrogenation using a commercially available Pd black powder catalyst has developed.
研究論文（学術雑誌）, 英語

Purification and Properties of the Luciferase from the Marine Ostracod Vargula hilgendorfii.
Koji Kobayashi; Yoshihiro Ohmiya; Daisaku Shinohala; Takuji Nabetani; Haruki Niwa
"Bioluminescence and Chemiluminescence," ed by J. F. Case, P. J. Herring, B. H. Robinson, S. H. D. Haddock, L. J. Kricka, and P. E. Stanley: World Scientific, Singapore, World Scientific, Singapore, 掲載ページ 87-90, 出版日 2001年, 査読付
研究論文（国際会議プロシーディングス）, 英語

Improved Syntheses of Watasenia Preluciferin (Coelenterazine) and Watasenia Luciferin (Coelenterazine Disulfate), and Site Specific Syntheses of the Coelenterazine Monosulfates.
Satoshi Kojima; Shojiro Maki; Takashi Hirano; Haruki Niwa; Mamoru Ohashi; Frederick I. Tsuji
ITE Letters on Batteries, New Technologies and Medicine, 2巻, 3号, 掲載ページ pp. C1-C5, 出版日 2001年, 査読付
研究論文（学術雑誌）, 英語

Intramolecular electron-transfer-induced cleavage of dioxetanes observed in fast-atom bombardment tandem mass spectrometry
M Ohashi; M Takanashi; N Watanabe; M Matsumoto; T Saisu; H Niwa
EUROPEAN JOURNAL OF MASS SPECTROMETRY, IM PUBLICATIONS, 7巻, 6号, 掲載ページ 441-445, 出版日 2001年, 査読付, Phenolic spiroadamantyl-substituted dioxetanes are well known base-induced chemiluminescent compounds. Fast-atom bombardment collision-induced dissociation tandem mass spectrometry (FAB CID-MS/MS) of five phenolic spiroadamantyl-substituted dioxetanes in the negative-ion mode clearly showed that a highly efficient cleavage of the dioxetane rings took place to produce the corresponding phenolate ion almost exclusively. The mass spectrometric behavior of these compounds reflects the highly efficient intramolecular electron-transfer-induced cleavage of dioxetane rings, which participates in the highly efficient base-triggered chemiluminescent reactions of these compounds in solution.
研究論文（学術雑誌）, 英語

Isoquinoline formation by a novel photochemical intermolecular cycloaddition of 1,1-diphenylethene derivatives to 1,4-dicyanobenzene
H Ishii; Y Imai; T Hirano; S Maki; H Niwa; M Ohashi
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 41巻, 33号, 掲載ページ 6467-6471, 出版日 2000年08月, 査読付, Phenanthrene-sensitized photoreaction of 1,1-diphenylethene (DPE) derivatives and 1,4-dicyanobenzene (DCNB) in benzene leads to a novel intermolecular cycloaddition to give isoquinoline derivatives as a novel synthetic method. The feasibility of this reaction was dependent upon the side chain structure of DPE derivatives, which would regulate the stability of radical cation DPE+. in a highly polar exciplex, and/or a contact radical ion pair, by hyperconjugation or neighboring group participation. (C) 2000 Elsevier Science Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

2,3,3a,4,9,9a-Hexahydro-9-phenyl-benzo[f]indene derivatives
D Hashizume; N Takashima; T Oikawa; H Ishii; H Niwa; F Iwasaki
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, MUNKSGAARD INT PUBL LTD, 56巻, 掲載ページ 827-829, 出版日 2000年07月, 査読付, The title compounds, 3a,9a-trans-9,9a-trans-4,4-dimethyl-9-phenyl-2,3,3a,4,9,9a-hexahydrobenzo[f]indene, C21H24, (I), and 3a,4-trans-3a,9a-cis-9,9a-trans-4-methoxy-9-phenyl-2,3,3a,4,9,9a-hexahydrobenzo[f]indene, C20H22 O, (II), are products of the photoinduced electron-transfer reaction of 1,1-diphenyl-1,n-alkadienes. The molecular structures are in good agreement with those proposed from the reaction mechanisms. The central rings of the fused systems of both compounds take chair and boat conformations in (I) and (II), respectively. There are no remarkable short contacts shorter than the sum of the van der Waals radii in the crystals, but some weak C-H ...pi interactions are found.
研究論文（学術雑誌）, 英語

Bioluminescence activity of Latia luciferin analogs
S Kojima; S Maki; T Hirano; Y Ohmiya; H Niwa
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 41巻, 22号, 掲載ページ 4409-4413, 出版日 2000年06月, 査読付, Latia luciferin analogs were synthesized and their bioluminescence activities were measured. The Latia luciferase was found to recognize strictly the 2,6,6-trimethylcyclohexene ring moiety in the luciferin structure. While the enol ether analogs exhibited no bioluminescence activity, the corresponding enol acetate analog possessed 60% activity compared to natural luciferin having an enol formate structure, implying that the initial step of the light producing reaction is an enzymatic hydrolysis to yield the corresponding enolate anion. (C) 2000 Elsevier Science Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry using an inorganic particle matrix for small molecule analysis
T Kinumi; T Saisu; M Takayama; H Niwa
JOURNAL OF MASS SPECTROMETRY, JOHN WILEY & SONS LTD, 35巻, 3号, 掲載ページ 417-422, 出版日 2000年03月, 査読付, Fine metal or metal oxide powder as an alternative to conventional organic matrices in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOFMS) has been utilized successfully for lower molecular mass analytes, poly(ethylene glycol) 200 (PEG 200) and methyl stearate. Eleven kinds of particle, Al, Mn, Mo, Si, Sn, SnO2, TiO2, W, WO3, Zn and ZnO, were evaluated. The analyte was mixed with a metal or metal oxide powder (inorganic matrix) with particle diameter of tens of micrometers and liquid dispersant, followed by application to the sample target. Using a commercial MALDI-TOFRMS instrument equipped with an internal 337 nm pulsed nitrogen laser, the analytes, PEG 200 and methyl stearate, were ionized as the alkali metal ion adducted molecules [hl + Na](+) or [M + K](+) when the inorganic matrices Mn, Mo, Si, Sn, TiO2, W, WO3, Zn or ZnO were used. In the case of an Al matrix, PEG 200 was ionized as [hl + K]+, whereas methyl stearate was ionized as [M + H](+) and [M + Al](+). These particles have potential as the matrix for MALDI. During our examination, however, only SnO2 particles did not ionize either PEG 200 or methyl stearate. Based on our protocol, when TiO2 powder was suspended with Liquid paraffin, PEG 200 and methyl stearate gave their MALDI-TOF mass spectra with the lowest background noise and highest intensity. TiO2 powder seemed to be a broad potential matrix for low molecular mass polar or non-polar analytes. The results suggested that bulk particles caused rapid heating/vaporization processes and ionized analyte molecules under irradiation with a pulsed W laser. The present method can be readily applied to obtain the low background noise MALDI-TOF mass spectra of small-sized compounds. Copyright (C) 2000 John Whey gi Sons, Ltd.
研究論文（学術雑誌）, 英語

Synthesis, chemi- and bioluminescence properties, and photolysis of a coelenterazine analogue having a photoreactive azido group
Jing Ling Zheng; Feng Qi Chen; Takashi Hirano; Yoshihiro Ohmiya; Shojiro Maki; Haruki Niwa; Mamoru Ohashi
Bulletin of the Chemical Society of Japan, 73巻, 2号, 掲載ページ 465-469, 出版日 2000年02月, 査読付, A photoreactive analogue of coelenterazine having an azido group was synthesized. The analogue showed similar chemi- and bioluminescence properties to those of the natural coelenterazine. Photolysis of the analogue in the presence of diethylamine gave a derivative azepine as the major product.
研究論文（学術雑誌）, 英語

Synthesis and Chemi-and Bio-luminescence Properties of a Photolabile Coelenterazine Analogue Bearing an Azido Group.
Zheng, J. L; Chen, F. Q; Hirano, T; Ohmiya, Y; Maki, S; Niwa, H; Ohashi, M
Bull. Chem. Soc. Jpn., 73巻, 2号, 掲載ページ pp. 465-469, 出版日 2000年, 査読付
研究論文（学術雑誌）, 英語

Differentiation Between N-Acetylchondrosine and N-Acetyldermosin by Matrix-assisted Laser Desorption Ionization Time-of-flight Post Source Decay Mass Spectrometry.
Mamoru Ohashi; Masami Araki; Takumi Saisu; Takuji Nabetani; Haruki Niwa
J. Mass Spectrom. Jpn., 48巻, 1号, 掲載ページ pp. 26-31, 出版日 2000年, 査読付
研究論文（学術雑誌）, 英語

Phosphopeptide sequencing by in-source decay spectrum in delayed extraction matrix-assisted laser desorption ionization time-of-flight mass spectrometry
T Kinumi; H Niwa; H Matsumoto
ANALYTICAL BIOCHEMISTRY, ACADEMIC PRESS INC, 277巻, 2号, 掲載ページ 177-186, 出版日 2000年01月, 査読付, Protein phosphorylation underlies numerous cellular signaling processes. Since a reliable prediction of phosphorylation site(s) based on a consensus amino acid sequence is rather difficult to date, determination of phosphorylation site(s) in phosphoproteins is a crucial step toward the understanding of their function at the molecular level. A conventional protocol for the determination of phosphorylation sites utilizes radioactive labeling of a phosphoprotein by P-32 and purification of digested peptides carrying radioactivity, followed by Edman degradation. This method is not only tedious, but also indirect because the evidence will be based on disappearance of a phenylthiohydantoin signal from the degradation cycle where the P-32 radioactivity is eluted, Several methodologies have been developed to determine the phosphorylation sites directly by using mass spectrometry. These include collision-induced dissociation (CLD) and post-source decay (PSD), both of which tend to produce fragment ions less efficiently as the number of residues exceeds 20, Moreover, in both decay processes, there is a tendency for the phosphate group to be removed during the breakdown of the main peptide chain. We report a method that allows direct observation of phosphorylated peptide fragments of phosphopeptides exceeding 20 residues by using an in-source decay fragmentation by matrix-assisted laser desorption ionization time-of-flight mass spectrometry, yielding results which are difficult or impossible to obtain by existing methods using CID or PSD. (C) Academic Press.
研究論文（学術雑誌）, 英語

Selective alkene hydrogenation with atomic hydrogen permeating through a Pd sheet electrode
S Maki; Y Harada; T Hirano; H Niwa; Y Yoshida; S Ogata; S Nakamatsu; H Inoue; C Iwakura
SYNTHETIC COMMUNICATIONS, TAYLOR & FRANCIS INC, 30巻, 19号, 掲載ページ 3575-3583, 出版日 2000年, 査読付, Chemoselective hydrogenation of olefinic double bonds without concomitant hydrogenolysis of allylic and benzylic C-O linkages was performed successfully by the aid of active hydrogen permeated through a Pd sheet electrode.
研究論文（学術雑誌）, 英語

Purification and Chracteristic Properties of the Luciferase from the Marine Ostracod Vargula hilgendorfii.
Koji Kobayashi; Daisaku Shinohara; Takuji Nabetani; Haruki Niwa; Yoshihiro Ohmiya
ITE Letters on Batteries, New Technologies & Medicine, 1巻, 3号, 掲載ページ pp. 422-426, 出版日 2000年, 査読付
研究論文（学術雑誌）, 英語

Reactivity and pi-facial selectivity of nucleophile addition to the radical cations of 7-benzhydrylidenenorbornene derivatives
H Ishii; S Shiina; T Hirano; H Niwa; M Ohashi
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 40巻, 3号, 掲載ページ 523-526, 出版日 1999年01月, 査読付, For correlating a homoconjugation structure of a radical cation to its reactivity with a nucleophile, the reactivity and pi-facial selectivity of CH3OH and H2O addition to the radical cations of 7-benzhydrylidenenorbornene derivatives generated by photoinduced electron transfer reactions were investigated. (C) 1998 Elsevier Science Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

Regiocontrolled construction of functionalized spiro[4,4]nonanones through mercury(II) salt-assisted and acid-induced spiroannulation reactions
Y Hashizume; S Maki; M Ohashi; H Niwa
SYNTHETIC COMMUNICATIONS, MARCEL DEKKER INC, 29巻, 7号, 掲載ページ 1223-1233, 出版日 1999年, 査読付, The mercuric(II)-assisted spiroannulation reactions of the enol silyl ethers derived from alpha-(4-pentynyl)-cyclopentanones 8a and 11 gave functionalized spiro[4.4]nonanones, exo-3 and exo-4, respectively, in moderate yields. On the other hand, the treatment of 8a and 8b with methanesulfonic acid provided endo-3 in high yield.
研究論文（学術雑誌）, 英語

Stereoselective tandem cyclization of 1,1-diphenyl-1,n-alkadienes via photoinduced electron transfer reaction
H Ishii; R Yamaoka; Y Imai; T Hirano; S Maki; H Niwa; D Hashizume; F Iwasaki; M Ohashi
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 39巻, 51号, 掲載ページ 9501-9504, 出版日 1998年12月, 査読付, The photoinduced electron transfer reaction of 1,1-diphenyl- 1,n-alkadienes in the presence of phenanthrene and 1,4-dicyanobenzene as a sensitizer and an electron acceptor, respectively gave intramolecular tandem cyclization products in highly stereocontrolled manner. (C) 1998 Elsevier Science Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

Synthesis of(±)-Isoitalicene using Electrolysis under Irradiation as a Key Step.
Yasuhiro Harada; Shojiro Maki; Takashi Hirano; Haruki Niwa; Shosuke Yamamura
Synlett, GEORG THIEME VERLAG, 12号, 掲載ページ 1313-1314, 出版日 1998年12月, 査読付, By utilizing electrolysis under irradiation, isoitalicene possessing a unique tricycle [5.4.0.0(1,5)] undec-8-ene skeleton was efficiently synthesized in high yield from a phenol derivative bearing an olefinic side chain.
研究論文（学術雑誌）, 英語

Synthesis of dimethyl gloiosiphone A
Y Hashizume; S Maki; M Ohashi; H Niwa
SYNLETT, GEORG THIEME VERLAG, 12号, 掲載ページ 1357-1358, 出版日 1998年12月, 査読付, A formal total synthesis of dimethyl gloiosiphone A (1) possessing a novel, densely oxygenated spiro[4.4]nonanedione framework was achieved starting with 6-methylenespiro[4.4]nonan-1-one.
研究論文（学術雑誌）, 英語

Bioluminescent properties of fluorinated semi-synthetic aequorins
Takashi Hirano; Yoshihiro Ohmiya; Shojiro Maki; Haruki Niwa; Mamoru Ohashi
Tetrahedron Letters, 39巻, 31号, 掲載ページ 5541-5544, 出版日 1998年07月30日, 査読付, Bioluminescent properties of semi-synthetic aequorins containing coelenterazine analogues possessing fluoro group(s) on the 6-(4- hydroxyphenyl) group match the fluorescent behavior of the phenolate anions of the corresponding fluorinated coelenteramide analogues, indicating that the phenolate anion of coelenteramide is the light-emitter in aequorin bioluminescence.
研究論文（学術雑誌）, 英語

A novel, stereoselective photo-Ritter reaction of 1,1-diphenyl-1,6-heptadiene via photoindnced electron transfer reaction
H Ishii; T Hirano; S Maki; H Niwa; M Ohashi
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 39巻, 18号, 掲載ページ 2791-2792, 出版日 1998年04月, 査読付, Irradiation of a wet acetonitrile nitrile solution of 1,1-diphenyl-1,6-heptadiene in the presence of 1,4-dicyanobenzene and phenanthrene provided cis-1-acetamido-3-(diphenylmethyl)cyclohexane in high yields with high stereoselectivity. Several examples leading to cis-1-acylamino-3-(diphenylmethyl)cyclohexanes were also described. (C) 1998 Elsevier Science Ltd. All rights reserved.
研究論文（学術雑誌）, 英語

"Fluorescent Properties of Model Chromophores of Tyrosine-66 Substituted Mutants of Aequorea Green Fluorescent Protein(GFP)"
Satoshi Kojima; Hiroko Ohkawa; Takashi Hirono; Haruki Niwa; Mamoru Ohashi; satoshi Inouye; Frederick I. Tsuji
Tetrahedron Letters, Elsevier Ltd., 39巻, 29号, 掲載ページ 5239-5242, 出版日 1998年, 査読付, GFPの発色団は６５−６７番目のSer-Tyr-Glyの間で形成する．近年，異なる蛍光性を示すGFP変異体GFP Y66F，GFP Y66Hなどが作製されているがその発色団構造に関する知見はない．本報告では各変異体に対応する発色団のモデル化合物を合成しその蛍光挙動を検討した．また，各変異体タンパクを発現させその蛍光スペクトルよりモデル化合物の構造の妥当性を明らかとした．
研究論文（学術雑誌）, 英語

Substituent effects on the chemiluminescent properties of coelenterazine analogues
R Saito; T Hirano; H Niwa; M Ohashi
CHEMISTRY LETTERS, CHEMICAL SOC JAPAN, 27巻, 1号, 掲載ページ 95-96, 出版日 1998年, 査読付, Chemiluminescence maxima and quantum yields sf coelenterazine analogues possessing a substituent R [= CF3, F, H, OCH3, OH, N(CH3)(2)] at the para-position on the 6-phenyl group were measured in DMSO, The result indicates that the variation of the electronic properties of R of these analogues caused the small change of the efficiency of chemical generation of a singlet excited light-emitter (Phi(S)).
研究論文（学術雑誌）, 英語

FAB-CID Mass Spectrometry of Imizdazplone DErivatives Related to the Chromophore of Green Fluorescent Potein in Jellyfish Bioluminescence.
Toshikazu Hiraki; Masayasu Kubota; Takashi Hirano; Haruki Niwa; Mamoru Ohashi
J. Mass Spectrom. Jpn., 46巻, 1号, 掲載ページ pp. 37-43, 出版日 1998年, 査読付
研究論文（学術雑誌）, 英語

Fluorescent Properties of Model Chromophores for the Mutant Proteins of Aequorea Green Fluorescent Protein(GFP).
Satoshi Kojima; Hiroko Ohkawa; Takashi Hirono; Haruki Niwa; Mamoru Ohashi; satoshi Inouye; Frederick I. Tsuji
Tetrahedron Lett., 39巻, 29号, 掲載ページ pp. 5239-5243, 出版日 1998年, 査読付
研究論文（学術雑誌）, 英語

Bioluminescent Properties of Fluorinated Semi-synthetic Aequorins : Structure Elucidation of the Light-emitter in Aequorin Bioluminescence.
Takashi Hirano; Yoshihiro Ohmiya; Shojiro Maki; Haruki Niwa; Mamoru Ohashi
Tetrahedron Lett., 39巻, 31号, 掲載ページ pp. 5541-5545, 出版日 1998年, 査読付
研究論文（学術雑誌）, 英語

FAB CID-MS/MS of In-source Fragment Ions as a Means to Differenciate Linkage Isomers of Branched Sugars : Le＾a＾ and Le＾x ＾Type Glycoconjugates.
Yoko Ohashi; Tadashi Ii; Masayasu Kubota; Shigeki Nunomura; Haruki Niwa; Mamoru Ohashi; Tomoyo Ogawa; Yoshitaka Nagai
J. Mass Spectrom. Jpn., The Mass Spectrometry Society of Japan, 46巻, 1号, 掲載ページ pp. 45-52, 出版日 1998年, 査読付, Here we report that FAB CID-MS/MS, choosing an ion originating from the in-source degradation prior to the full acceleration of the molecule-related ion as the precursor, is an excellent means to differentiate linkage isomers. FAB CID-MS/MS performed in this way results in a product ion spectrum, which is enriched with the fragmentation information, and which may thus indicate the position of the newly formed OH group already produced in the ion source. Linkage knowledge may be classified into one of three categories as described later. This method was applied to acidic Lewis-type glycoconjugates —putative ligands for selectins [L. L. W. Cooling, D.-S. Zhang, and T. A. W. Koerner, Trends in Glycosci. Glycotech., 9, 191 (1997)]— and their neutral analogs to differentiate linkage isomers by mass spectrometry. With these glycoconjugates FAB CID-MS/MS having [M+H]⁺s as the precursor ions is a good means to distinguish the linkage isomers only in simple cases, but not in general cases. By using ions originating from in-source degradation prior to the full acceleration of the molecule-related ion as the precursor, we were able to differentiate between Le^a and Le^x.
研究論文（学術雑誌）, 英語

Novel dehydration reaction of neoanisatin and transformation of neoanisatin into anisatin
J Yoshizawa; K Obitsu; S Maki; H Niwa; T Hirano; M Ohashi
SYNLETT, GEORG THIEME VERLAG, 12号, 掲載ページ 1387-1388, 出版日 1997年12月, 査読付, Reaction of neoanisatin with methyl oxalyl chloride in pyridine gave a novel dehydration product, from which anisatin was prepared.
研究論文（学術雑誌）, 英語

Facile cleavage reactions of styrylic olefins using electrochemical methods
S Maki; H Niwa; T Hirano
SYNLETT, GEORG THIEME VERLAG, 12号, 掲載ページ 1385-1386, 出版日 1997年12月, 査読付, Negative constant current electrolysis of styrylic olefins in an aqueous solvent resulted in the oxidative cleavage of the double bonds, giving carbonyl compounds in good yields. The double bond conjugated with more than one aromatic ring was selectively cleaved.
研究論文（学術雑誌）, 英語

An efficient synthesis of racemic necine bases from a common intermediate
H Niwa; A Kuroda; T Sakata; K Yamada
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOC JAPAN, 70巻, 10号, 掲載ページ 2541-2543, 出版日 1997年10月, 査読付, Necine bases of pyrrolizidine alkaloids, turneforcidine, hastanecine, and platynecine are synthesized from ethyl 1-hydroxy-2,3,5,6-tetrahydro-1H-pyrrolizine-7-carboxylate in racemic form.
研究論文（学術雑誌）, 英語

Solvent and substituent effects on the fluorescent properties of coelenteramide analogues
R Saito; T Hirano; H Niwa; M Ohashi
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, ROYAL SOC CHEMISTRY, 9号, 掲載ページ 1711-1716, 出版日 1997年09月, 査読付, Coelenteramide 1 is the light emitter in aequorin bioluminescence. To establish the fluorescent character of 1, the fluorescence properties of 1 and a series of its analogues, 3a-f, possessing a substituent R [= CF3, F, H, OCH3, OH, N(CH3)(2)] at the para-position on the 5-phenyl group have been investigated in solvents of various polarity. The fluorescence emission maxima of 1 and 3d-f, possessing an electron-donating group R [= OCH3, OH, N(CH3)(2)] shift to lower energy with increasing solvent polarity, while those of the analogues 3a-c (R = CF3, F, H) are independent of the solvent polarity. The linear correlation between the fluorescence maxima of 1 and 3d-f and the solvent polarity scales can be explained by formation of the singlet excited state with a charge-transfer (CT) character. The quantum yields of CT fluorescence of 1 and 3d-f have been found to be higher than those of 3a-c. These results indicate that the solvatochromic fluorescence of 1 originates from the CT excited state and the existence of an electron donating hydroxy group on the 5-phenyl group is essential for determining a wavelength and a high fluorescence quantum yield of aequorin bioluminescence.
研究論文（学術雑誌）, 英語

Abnormal reactivity of anisatin and neoanisatin to samarium iodide hexamethylphosphorictriamide
K Obitsu; S Maki; H Niwa; T Hirano; M Ohashi
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 38巻, 23号, 掲載ページ 4111-4112, 出版日 1997年06月, 査読付, Reactions of anisatin and neoanisatin with SmI2 in the presence of HMPA give novel products having an oxaadamanthane skeleton accompanied by decarboxylation from the spiro beta-lactone functionality. (C) 1997 Elsevier Science Ltd.
研究論文（学術雑誌）, 英語

Mechanism of the redox reaction of the Aequorea green fluorescent protein (GFP)
S Kojima; T Hirano; H Niwa; M Ohashi; S Inouye; FL Tsuji
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 38巻, 16号, 掲載ページ 2875-2878, 出版日 1997年04月, 査読付, A model compound, 4-(4-hydroxyphenyl)methylideneimidazol-5-one undergoes a reversible redox reaction identical to that of the Aequorea green fluorescent protein (GFP), strongly suggesting that the GFP chromophore is derived via the autoxidation of a nonfluorescent dihydro precursor in dihydro-GFP. (C) 1997 Elsevier Science Ltd.
研究論文（学術雑誌）, 英語

Aequorea green fluorescent protein: Structural elucidation of the chromophore
H Niwa; T Matsuno; S Kojima; M Kubota; T Hirano; M Ohashi; S Inouye; Y Ohmiya; FI Tsuji
BIOLUMINESCENCE AND CHEMILUMINESCENCE, JOHN WILEY & SONS LTD, 掲載ページ 395-398, 出版日 1997年, 査読付
研究論文（国際会議プロシーディングス）, 英語

Chemical nature of the light emitter of the Aequorea green fluorescent protein
H Niwa; S Inouye; T Hirano; T Matsuno; S Kojima; M Kubota; M Ohashi; FI Tsuji
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, NATL ACAD SCIENCES, 93巻, 24号, 掲載ページ 13617-13622, 出版日 1996年11月, 査読付, The jellyfish Aequorea victoria possesses in the margin of its umbrella a green fluorescent protein (GFP, 27 kDa) that serves as the ultimate light emitter in the bioluminescence reaction of the animal, The protein is made up of 238 amino acid residues in a single polypeptide chain and produces a greenish fluorescence (lambda(max) = 508 nm) when irradiated with long ultraviolet light. The fluorescence is due to the presence of a chromophore consisting of an imidazolone ring, formed by a post-translational modification of the tripeptide -Ser(65)-Tyr(66)-Gly(67)-. GFP has been used extensively as a reporter protein for monitoring gene expression in eukaryotic and prokaryotic cells, but relatively little is known about the chemical mechanism by which fluorescence is produced, To obtain a better understanding of this problem, we studied a peptide fragment of GFP bearing the chromophore and a synthetic model compound of the chromophore, The results indicate that the GFP chromophore consists of an imidazolone ring structure and that the light emitter is the singlet excited state of the phenolate anion of the chromophore, Further, the light emission is highly dependent on the microenvironment around the chromophore and that inhibition of isomerization of the exo-methylene double bond of the chromophore accounts for its efficient light emission.
研究論文（学術雑誌）, 英語

Unusual reactions of C-60 with aldehydes in the presence of aqueous ammonia
A Komori; M Kubota; T Ishida; H Niwa; T Nogami
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 37巻, 23号, 掲載ページ 4031-4034, 出版日 1996年06月, 査読付, Fullerene C-60 reacts with alkylaldehydes in the presence of aqueous ammonia to give 2,5-dialkyl-substituted pyrrolidine derivatives. The reaction of phenylacetaldehyde under similar conditions afforded C-60(H)(CH(2)Ph) via possible decarbonylation. On the basis of the product analysis, reaction mechanisms are proposed in which C-60 plays the role of a dipolarophile or radical scavenger. (C) 1996 Elsevier Science Ltd.
研究論文（学術雑誌）, 英語

A POTENTIAL PHOTOAFFINITY PROBE FOR LABELING THE ACTIVE-SITE OF AEQUORIN - A PHOTOLABILE COELENTERAZINE ANALOG WITH A TRIFLUOROMETHYLDIAZIRINE GROUP
FQ CHEN; JL ZHENG; T HIRANO; H NIWA; Y OHMIYA; M OHASHI
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, ROYAL SOC CHEMISTRY, 17号, 掲載ページ 2129-2134, 出版日 1995年09月, 査読付, In order to clarify the active site of aequorin, we have: successfully synthesized a photolabile analogue of coelenterazine with a trifluoromethyldiazirine group as a photoaffinity probe. Our studies on the chemi- and bio-luminescence of this novel analogue indicate that its behaviour is almost identical with that of natural coelenterazine in terms of luminescence characteristics. Therefore, the analogue with the photolabile diazirine should be a useful photoaffinity label for probing the detailed structure of aequorin.
研究論文（学術雑誌）, 英語

ENANTIOSELECTIVE SYNTHESIS OF THE MACROCYCLIC PYRROLIZIDINE ALKALOID YAMATAIMINE
H NIWA; K KUNITANI; T NAGOYA; K YAMADA
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOC JAPAN, 67巻, 11号, 掲載ページ 3094-3099, 出版日 1994年11月, 査読付, Described is a short-step synthesis of optically active yamataimine, a 12-membered pyrrolizidine alkaloid of retronecine type. Methyl (1S,SR)-5-methyl-2-oxocyclopentanecarboxylate derived from (R)-(+)-pulegone was converted into the necic acid component required for the synthesis of yamataimine, in a nine-step sequence. Regioselective coupling of (+)-retronecine with the necic acid component via tin-mediated regioselective acylation followed by macrolactonization led to the first synthesis of (+)-yamataimine.
研究論文（学術雑誌）, 英語

An Improved Syntheis of(±)-Otonecine and a Synthesis of a 12-Memebered Otonecine Diester.
Haruki Niwa; Tomoyo Sakata; Kiyoyuki Yamada
Bull. Chem. Soc. Jpn., CHEMICAL SOC JAPAN, 67巻, 8号, 掲載ページ 2345-2347, 出版日 1994年08月, 査読付, (+/-)-4-Methyl-1-phenylthio-8-oxa-4-azabicyclo[5.2.1]decane-9,10-dione was efficiently converted into (+/-)-otonecine, which was regioselectively coupled with (E)-2-ethylidenehexanedioic acid to give a 12-membered otonecine diester.
研究論文（学術雑誌）, 英語

A SYNTHESIS OF SENECIONINE, A REPRESENTATIVE OF HEPATOTOXIC, MACROCYCLIC PYRROLIZIDINE ALKALOIDS OF RETRONECINE TYPE
H NIWA; T SAKATA; K YAMADA
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOC JAPAN, 67巻, 7号, 掲載ページ 1990-1993, 出版日 1994年07月, 査読付, Described is a synthesis of (-)-senecionine, the best-known hepatotoxic, 12-membered pyrrolizidine alkaloid of retronecine type. Integerrinecic acid lactone methyl ester was converted into protected senecic acid, which was regioselectively coupled with (+)-retronecine, achieving the first synthesis of (-)-senecionine.
研究論文（学術雑誌）, 英語

DIDEMNILACTONE-A AND DIDEMNILACTONE-B AND NEODIDEMNILACTONE, 3 NEW FATTY-ACID METABOLITES ISOLATED FROM THE TUNICATE DIDEMNUM MOSELEYI (HERDMAN)
H NIWA; M WATANABE; H INAGAKI; K YAMADA
TETRAHEDRON, PERGAMON-ELSEVIER SCIENCE LTD, 50巻, 25号, 掲載ページ 7385-7400, 出版日 1994年06月, 査読付, Three new fatty acid metabolites didemnilactones A (1) and B (2) and neodidemnilactone (3) were isolated from the tunicate Didemnum moseleyi (Herdman). Their structures including absolute stereochemistry were established on the basis of spectral studies and chemical synthesis. Didemnilactones exhibited inhibitory activity against lipoxygenase and weak binding activity to leukotriene B-4 receptors.
研究論文（学術雑誌）, 英語

Structures of monodontamides A, B, C, D, E, and F, six new alkaloids isolated from the marine gastropod mollusc Monodonta labio (Linné)
Haruki Niwa; Masaru Watanabe; Atsushi Sano; Kiyoyuki Yamada
Tetrahedron, 50巻, 23号, 掲載ページ 6805-6818, 出版日 1994年, 査読付, Six new alkaloids monodontamides A (1), B (2), C (3), D (4), E (5), and F (6) were isolated from the marine gastropod mollusc Monodonta labio (Linné). The structures of monodontamides were established on the basis of spectral data and unambiguous synthesis. Monodontamides exhibited weak inhibitory activity against a serine protease. © 1994.
研究論文（学術雑誌）, 英語

Monodontamides A, B, and C, three new putrescine alkaloids from the marine gastropod mollusc Monodonta labio (Linné)
Haruki Niwa; Masaru Watanabe; Kiyoyuki Yamada
Tetrahedron Letters, 34巻, 46号, 掲載ページ 7441-7444, 出版日 1993年11月12日, 査読付, Described are the structure determination and synthesis of three new alkaloids, monodontamides A (1), B (2), and C (3) isolated from the marine gastropod mollusc Monodonta labio (Linné). © 1993.
研究論文（学術雑誌）, 英語

TOTAL SYNTHESIS OF NATURAL (-)-PTAQUILOSIN, THE AGLYCON OF A POTENT BRACKEN CARCINOGEN PTAQUILOSIDE, AND THE (+)-ENANTIOMER AND THEIR DNA CLEAVING ACTIVITIES
H KIGOSHI; Y IMAMURA; K MIZUTA; H NIWA; K YAMADA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMER CHEMICAL SOC, 115巻, 8号, 掲載ページ 3056-3065, 出版日 1993年04月, 査読付, The total synthesis of natural (-)-ptaquilosin (2) the aglycon of a potent carcinogen ptaquiloside (1) from bracken fern and its (+)-enantiomer (2) has been achieved starting with (+)-dimenthyl (1R,2R)-cyclopentane-1,2-dicarboxylate. The synthesis proceeds in 20 steps (2.9% overall yield). The key features of the synthesis are as follows: (i) diastereoselective alkylation of a common chiral compound 5 under different conditions has provided each of two diastereomers 6a and 6b predominantly, the former 6a eventually leading to natural (-)-2 and the latter 6b giving unnatural (+)-2 and (ii) the deformylative oxidation reaction of aldehyde 23 has been effected under the conditions mild enough to permit survival of the unstable product ptaquilosin (2). As to the DNA cleaving activities, dienone 4 prepared from natural (-)-ptaquilosin (2) was shown to be more efficient than dienone 4 derived from unnatural (+)-ptaquilosin (2).
研究論文（学術雑誌）, 英語

AN EFFICIENT ENANTIOSELECTIVE SYNTHESIS OF INDICINE N-OXIDE, AN ANTITUMOR PYRROLIZIDINE ALKALOID
T OGAWA; H NIWA; K YAMADA
TETRAHEDRON, PERGAMON-ELSEVIER SCIENCE LTD, 49巻, 8号, 掲載ページ 1571-1578, 出版日 1993年02月, 査読付, Indicine N-oxide (1), a pyrrolizidine alkaloid potentially useful for an anticancer drug was synthesized in the natural form through regioselective coupling of (+)-retronecine (2) and the protected necic acids 16a and 16b, the latter being efficiently prepared from the optically pure lactone 5.
研究論文（学術雑誌）, 英語

TOTAL SYNTHESIS OF OPTICALLY-ACTIVE MONOCROTALINE, A CARCINOGENIC PYRROLIZIDINE ALKALOID POSSESSING AN 11-MEMBERED RETRONECINE DILACTONE
H NIWA; T OGAWA; O OKAMOTO; K YAMADA
TETRAHEDRON, PERGAMON-ELSEVIER SCIENCE LTD, 48巻, 48号, 掲載ページ 10531-10548, 出版日 1992年11月, 査読付, A total synthesis of the natural enantiomer of monocrotaline (1), a representative of carcinogenic pyrrolizidine alkaloids having an 11-membered retronecine dilactone was achieved through regioselective coupling of (+)-retronecine (3) and the optically active protected necic acid 8, the latter being prepared enantioselectively from the meso-diester 11.
研究論文（学術雑誌）, 英語

TOTAL SYNTHESIS OF OPTICALLY-ACTIVE INTEGERRIMINE, A 12-MEMBERED DILACTONIC PYRROLIZIDINE ALKALOID OF RETRONECINE TYPE
H NIWA; Y MIYACHI; O OKAMOTO; Y UOSAKI; A KURODA; H ISHIWATA; K YAMADA
TETRAHEDRON, PERGAMON-ELSEVIER SCIENCE LTD, 48巻, 3号, 掲載ページ 393-412, 出版日 1992年01月, 査読付, A total synthesis of the natural enantiomer of integerrimine (1), a twelve-membered dilactonic pyrrolizidine alkaloid of retronccine type has been achieved through the enantioselective synthesis and regioselective coupling of (+)-retronecine (4) and (+)-integerrinecic acid (methylthio)methyl ether (6).
研究論文（学術雑誌）, 英語

NOVEL TRANSFORMATION OF FORMYL GROUPS INTO HYDROXYL-GROUPS UTILIZING DEFORMYLATIVE AUTOXIDATION OF ALDEHYDES
H KIGOSHI; Y IMAMURA; A SAWADA; H NIWA; K YAMADA
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOC JAPAN, 64巻, 12号, 掲載ページ 3735-3737, 出版日 1991年12月, 査読付, Structural requirements that cause deformylative autoxidation of aliphatic aldehydes are investigated. Decarbonylation of acyl radicals proceeds smoothly when the alkyl radicals that are formed can be stabilized by allylic conjugation. Further conjugation of the double bond in the allyl radical with a carbonyl or a cyclopropyl group allows position-selective peroxidation of the alkyl radical.
研究論文（学術雑誌）, 英語

Further Chemical Studies on Anisatin, a Neurotoxic Sesquiterpenoid Having a β-Lactone.
Haruki Niwa; Itaru Tsukada; Masanori Nisiwaki; Kiyoyuki Yamada
Bull. Chem. Soc. Jpn., CHEMICAL SOC JAPAN, 64巻, 9号, 掲載ページ 2860-2862, 出版日 1991年09月, 査読付, By a series of chemical reactions, anisatin was efficiently converted into the key intermediate employed in the synthesis of anisatin.
研究論文（学術雑誌）, 英語

DIDEMNILACTONE AND NEODIDEMNILACTONE, 2 NEW FATTY-ACID METABOLITES POSSESSING A 10-MEMBERED LACTONE FROM THE TUNICATE DIDEMNUM-MOSELEYI (HERDMAN)
H NIWA; H INAGAKI; K YAMADA
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 32巻, 38号, 掲載ページ 5127-5128, 出版日 1991年09月, 査読付, Didemnilactone (1) and neodidemnilactone (2), two new fatty acid metabolites possessing a 10-membered lactone were isolated from the colonial tunicate Didemnum moseleyi (Herdman). Their structures including absolute stereochemistry were determined on the basis of spectral studies and the enantioselective synthesis of the antipode of 2.
研究論文（学術雑誌）, 英語

FACTORS THAT CAUSE CONTRASTERIC ALKYLATION OF A CYCLOPENTANE-1,2-DICARBOXYLIC ACID MONOESTER
H KIGOSHI; Y IMAMURA; K YOSHIKAWA; H NIWA; K YAMADA
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 32巻, 35号, 掲載ページ 4541-4544, 出版日 1991年08月, 査読付, The stereochemical outcome in the alkylation of the enolate generated from a cyclopentane-1,2-dicarboxylic acid monoester is described. The alkylation of the Li enolate with an alkylating reagent having a hard leaving group such as Cl gave a contrasteric alkylation (alkylation from the more hindered side of the enolate) product, predominantly. An important factor effecting contrasteric alkylation was found to be complexation of the hard leaving group of the alkylating reagent to the carboxylate Li counterion in the enolate.
研究論文（学術雑誌）, 英語

THE 3-DIMENSIONAL STRUCTURE OF NEOHALICHOLACTONE, AN UNUSUAL FATTY-ACID METABOLITE FROM THE MARINE SPONGE HALICHONDRIA-OKADAI KADOTA
H KIGOSHI; H NIWA; K YAMADA; TJ STOUT; J CLARDY
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 32巻, 22号, 掲載ページ 2427-2428, 出版日 1991年05月, 査読付, The three-dimensional structure of the unusual fatty acid metabolite neohalicholactone, isolated from the marine sponge Halichondria okadai Kadota, has been determined by X-ray crystallography.
研究論文（学術雑誌）, 英語

Synthesis of(-)-Neoanisatin, a Neurotoxic Sesquiterpenoid Having a Novel Spiro β-Lactone.
Haruki Niwa; Kiyoyuki Yamada
Chem. Letters, CHEMICAL SOC JAPAN, 20巻, 4号, 掲載ページ 639-640, 出版日 1991年04月, 査読付, (-)-Anisatin can be converted into (-)-neoanisatin, which accomplishes the total synthesis of the natural enantiomer of neoanisatin.
研究論文（学術雑誌）, 英語

Synthesis of(-)-Noranisatin, an Oxidation Product of a Neurotoxic Sesquiterpenoid Anisatin Having a Novel Spiro β-Lactone.
Haruki Niwa; Shigeki Ito; Takashi Hasegawa; Kazumasa Wakamatsu; Tatsuya Mori; Kiyoyuki Yamada
Tetrahedron Letters, PERGAMON-ELSEVIER SCIENCE LTD, 32巻, 10号, 掲載ページ 1329-1330, 出版日 1991年03月, 査読付, The synthesis of (-)-noranisatin (2), an oxidation product of anisatin (1) possessing a novel spiro beta-lactone, was achieved starting from triol 5 prepared from (R)-(+)-pulegone (3).
研究論文（学術雑誌）, 英語

Total Synthesis of(±)-(Z)-9-(Bromomethylene)-1,5,5-trimethylspiro[5.5]undeca-1,7-dien-3-one, a Brominated Sesquiterpene of the Chamigrane Type.
Haruki Niwa; Yoshifumi Yoshida; Takashi Hasegawa; Kiyoyuki Yamada
Tetrahedron, PERGAMON-ELSEVIER SCIENCE LTD, 47巻, 12-13号, 掲載ページ 2155-2162, 出版日 1991年03月, 査読付, (+/-)-(Z)-9-(Bromomethylene)-1,5,5-trimethylspirol[5.5]undeca-1,7-dien-3-one (1), a chamigrane sesquiterpene having a novel bromomethylene group is synthesized from anisole via spiroannelation of 4-(1,1-dimethyl-4-formylbutyl)-3-cyclohexen-1-one (10).
研究論文（学術雑誌）, 英語

ALKYLATION OF NUCLEOSIDES BY DEHYDROMONOCROTALINE, THE PUTATIVE TOXIC METABOLITE OF THE CARCINOGENIC PYRROLIZIDINE ALKALOID MONOCROTALINE
H NIWA; T OGAWA; O OKAMOTO; K YAMADA
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 32巻, 7号, 掲載ページ 927-930, 出版日 1991年02月, 査読付, Reaction of dehydromonocrotaline (3), the putative toxic metabolite of the carcinogenic pyrrolizidine alkaloid monocrotaline (2), with various nucleosides proceeded mostly at the C-9'' position of 3 to give several nitrogen atom-alkylated nucleosides including N-7 alkylated 2'-deoxyguanosine 14.
研究論文（学術雑誌）, 英語

ON THE MECHANISM OF THE CLEAVAGE REACTION OF (METHYLTHIO)METHYL ETHER WITH TRIPHENYLMETHYL CATION
H NIWA; Y MIYACHI
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOC JAPAN, 64巻, 2号, 掲載ページ 716-718, 出版日 1991年02月, 査読付, The cleavage reaction of a (methylthio)methyl (MTM) ether with triphenylmethyl cation was not initiated by the previously proposed hydride abstraction with triphenylmethyl cation but promoted by the coordination of triphenylmethyl cation as a Lewis acid to the sulfur atom in the MTM group.
研究論文（学術雑誌）, 英語

STEREOSELECTIVE SYNTHESIS OF (-)-TRACHELANTHIC ACID AND (+)-VIRIDIFLORIC ACID, NECIC ACID COMPONENTS OF PYRROLIZIDINE ALKALOIDS FROM A COMMON INTERMEDIATE
H NIWA; T OGAWA; K YAMADA
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOC JAPAN, 63巻, 12号, 掲載ページ 3707-3709, 出版日 1990年12月, 査読付, Diastereoselective reduction of a side-chain keto group in (2S,5R)-5-acetyl-2-(t-butyl)-5-isopropyl-1,3-dioxolan-4-one (5) with (i-Bu)2A1H in ether afforded (1'S,2S,5R)-2-(t-butyl)-5-(1'-hydroxyethyl)-5-isopropyl-1,3-dioxolan-4-one (6), while reduction of 5 with LiBH(s-Bu)3 in ether gave the (1'R)-isomer 7 predominantly. (-)-Trachelanthic acid (1) and (+)-viridifloric acid (2) were synthesized upon hydrolysis of 6 and 7, respectively.
研究論文（学術雑誌）, 英語

Stereocontrolled Total Synthesis of(-)-Anisatin : A Neurotoxic Sesquiterpenoid Possessing a Novel Spiro β-Lactone.
Haruki Niwa; Masanori Nisiwaki; Itaru Tsukada; Takeshi Ishigaki; Shigeki Ito; Kazumasa Wakamatsu; Tatsuya Mori; Megumi Ikagawa; Kiyoyuki Yamada
J. Am. Chem. Soc., AMER CHEMICAL SOC, 112巻, 24号, 掲載ページ 9001-9003, 出版日 1990年11月, 査読付
研究論文（学術雑誌）, 英語

A Biogenetic-Type Synthesis of(±)-Aplysiadiol, a Brominated Diterpene Isolated from the Marine Mollusc Aplysia kurodai.
Haruki Niwa; Shigeru Ieda; Hideaki Inagaki; Kiyoyuki Yamada
Tetrahedron Letters, PERGAMON-ELSEVIER SCIENCE LTD, 31巻, 49号, 掲載ページ 7157-7158, 出版日 1990年, 査読付
研究論文（学術雑誌）, 英語

ACUTE MICROCIRCULATORY CHANGES INDUCED BY INTRAVENOUS ADMINISTRATION TO RABBITS OF PTAQUILOSIDE, A BRACKEN CARCINOGEN
M ASANO; C OHKUBO; A SASAKI; HIRONO, I; K YAMADA; H NIWA; M OJIKA
JOURNAL OF ETHNOPHARMACOLOGY, ELSEVIER SCI IRELAND LTD, 27巻, 1-2号, 掲載ページ 213-220, 出版日 1989年11月, 査読付
研究論文（学術雑誌）, 英語

SYNTHESIS OF A FUNCTIONALIZED CARBOCYCLIC SKELETON OF PTAQUILOSIN, THE AGLYCONE OF A BRACKEN CARCINOGEN PTAQUILOSIDE BASED ON AN INTRAMOLECULAR DIELS-ALDER REACTION
H KIGOSHI; A SAWADA; H NIWA; K YAMADA
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOC JAPAN, 62巻, 5号, 掲載ページ 1639-1642, 出版日 1989年05月, 査読付
研究論文（学術雑誌）, 英語

TOTAL SYNTHESIS OF PTAQUILOSIN - THE AGLYCON OF PTAQUILOSIDE, A POTENT BRACKEN CARCINOGEN
H KIGOSHI; Y IMAMURA; H NIWA; K YAMADA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMER CHEMICAL SOC, 111巻, 6号, 掲載ページ 2302-2303, 出版日 1989年03月, 査読付
研究論文（学術雑誌）, 英語

Stereocontrolled Total Synthesis of(±)-Ptaquilosin, the Aglycone of Ptaquiloside, a Bracken Carcinogen.
Hideo Kigoshi; Akihiko Sawada; Yoshisuke Nakayama; Haruki Niwa; Kiyoyuki Yamada
Tetrahedron Letters, PERGAMON-ELSEVIER SCIENCE LTD, 30巻, 15号, 掲載ページ 1983-1986, 出版日 1989年, 査読付
研究論文（学術雑誌）, 英語

PTAQUILOSIN, THE AGLYCONE OF A BRACKEN CARCINOGEN PTAQUILOSIDE - CHEMICAL DERIVATION FROM PTAQUILOSIDE AND THE REACTIVITY
H KIGOSHI; A SAWADA; Y IMAMURA; H NIWA; K YAMADA
TETRAHEDRON, PERGAMON-ELSEVIER SCIENCE LTD, 45巻, 9号, 掲載ページ 2551-2556, 出版日 1989年, 査読付
研究論文（学術雑誌）, 英語

HALICHOLACTONE AND NEOHALICHOLACTONE, 2 NOVEL FATTY-ACID METABOLITES FROM THE MARINE SPONGE HALICHONDRIA-OKADAI KADOTA
H NIWA; K WAKAMATSU; K YAMADA
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 30巻, 34号, 掲載ページ 4543-4546, 出版日 1989年, 査読付
研究論文（学術雑誌）, 英語

AN EFFICIENT ENANTIOSELECTIVE SYNTHESIS OF (+)-INDICINE N-OXIDE, AN ANTITUMOR PYRROLIZIDINE ALKALOID
H NIWA; T OGAWA; K YAMADA
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 30巻, 37号, 掲載ページ 4985-4986, 出版日 1989年, 査読付
研究論文（学術雑誌）, 英語

A TIN-MEDIATED ONE-STEP SYNTHESIS OF (+)-DICROTALINE, AN 11-MEMBERED DILACTONIC PYRROLIZIDINE ALKALOID
H NIWA; O OKAMOTO; H ISHIWATA; A KURODA; Y UOSAKI; K YAMADA
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOC JAPAN, 61巻, 8号, 掲載ページ 3017-3019, 出版日 1988年08月, 査読付
研究論文（学術雑誌）, 英語

A BROMINATED QUINAZOLINEDIONE FROM THE MARINE TUNICATE PYURA-SACCIFORMIS
H NIWA; Y YOSHIDA; K YAMADA
JOURNAL OF NATURAL PRODUCTS, AMER SOC PHARMACOGNOSY, 51巻, 2号, 掲載ページ 343-344, 出版日 1988年03月, 査読付
研究論文（学術雑誌）, 英語

TOTAL SYNTHESIS OF OPTICALLY-ACTIVE MONOCROTALINE, A CARCINOGENIC PYRROLIZIDINE ALKALOID HAVING AN 11-MEMBERED DILACTONE
H NIWA; O OKAMOTO; K YAMADA
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 29巻, 40号, 掲載ページ 5139-5142, 出版日 1988年, 査読付
研究論文（学術雑誌）, 英語

AN EFFICIENT ENANTIOSELECTIVE SYNTHESIS OF THE (-)-N-(ETHOXYCARBONYL)METHYL GEISSMAN-WAISS LACTONE - A PRACTICAL SYNTHETIC ROUTE TO (+)-RETRONECINE
H NIWA; O OKAMOTO; Y MIYACHI; Y UOSAKI; K YAMADA
JOURNAL OF ORGANIC CHEMISTRY, AMER CHEMICAL SOC, 52巻, 13号, 掲載ページ 2941-2943, 出版日 1987年06月, 査読付
研究論文（学術雑誌）, 英語

ISOLATION OF THE STRAINED BRIDGEHEAD ENOL ETHER OF A BICYCLO[3.3.1]NONAN-2-ONE SYSTEM
K WAKAMATSU; H TAN; N BAN; N UCHIYAMA; H NIWA; K YAMADA
CHEMISTRY LETTERS, CHEMICAL SOC JAPAN, 16巻, 1号, 掲載ページ 121-122, 出版日 1987年, 査読付
研究論文（学術雑誌）, 英語

Stereocontrolled Total Synthesis of(±)-Norpatchoulenol and Two Metabolites of Patchouli Alcohol, (±)-Hydroxy Patchouli Alcohol and the Corresponding(±)-Carboxylic Acid.
Haruki Niwa; Takashi Hasegawa; Norikazu Ban; Kiyoyuki Yamada
Tetrahedron, PERGAMON-ELSEVIER SCIENCE LTD, 43巻, 5号, 掲載ページ 825-834, 出版日 1987年, 査読付
研究論文（学術雑誌）, 英語

PTAQUILOSIDE, A POTENT CARCINOGEN ISOLATED FROM BRACKEN FERN PTERIDIUM-AQUILINUM VAR LATIUSCULUM - STRUCTURE ELUCIDATION BASED ON CHEMICAL AND SPECTRAL EVIDENCE, AND REACTIONS WITH AMINO-ACIDS, NUCLEOSIDES, AND NUCLEOTIDES
M OJIKA; K WAKAMATSU; H NIWA; K YAMADA
TETRAHEDRON, PERGAMON-ELSEVIER SCIENCE LTD, 43巻, 22号, 掲載ページ 5261-5274, 出版日 1987年, 査読付
研究論文（学術雑誌）, 英語

STRUCTURES OF NEW P-HYDROXYSTYRENE GLYCOSIDES, PTELATOSIDE-A AND PTELATOSIDE-B ISOLATED FROM BRACKEN FERN, PTERIDIUM-AQUILINUM VAR LATIUSCULUM, AND SYNTHESIS OF PTELATOSIDE-A
M OJIKA; K WAKAMATSU; H NIWA; K YAMADA
TETRAHEDRON, PERGAMON-ELSEVIER SCIENCE LTD, 43巻, 22号, 掲載ページ 5275-5280, 出版日 1987年, 査読付
研究論文（学術雑誌）, 英語

STEREOCONTROLLED SYNTHESIS OF POLYFUNCTIONALIZED TRANS-HYDRINDAN SYSTEMS - A MODEL STUDY TOWARD ANISATIN
H NIWA; T MORI; T HASEGAWA; K YAMADA
JOURNAL OF ORGANIC CHEMISTRY, AMER CHEMICAL SOC, 51巻, 7号, 掲載ページ 1015-1018, 出版日 1986年04月, 査読付
研究論文（学術雑誌）, 英語

4 NEW C-15 ACETYLENIC POLYENES OF BIOGENETIC SIGNIFICANCE FROM THE RED ALGA LAURENCIA-OKAMURAI - STRUCTURES AND SYNTHESIS
H KIGOSHI; Y SHIZURI; H NIWA; K YAMADA
TETRAHEDRON, PERGAMON-ELSEVIER SCIENCE LTD, 42巻, 14号, 掲載ページ 3781-3787, 出版日 1986年, 査読付
研究論文（学術雑誌）, 英語

ISOLATION OF (10R,11R)-(+)-SQUALENE-10,11-EPOXIDE FROM THE RED ALGA LAURENCIA-OKAMURAI AND ITS ENANTIOSELECTIVE SYNTHESIS
H KIGOSHI; M OJIKA; Y SHIZURI; H NIWA; K YAMADA
TETRAHEDRON, PERGAMON-ELSEVIER SCIENCE LTD, 42巻, 14号, 掲載ページ 3789-3792, 出版日 1986年, 査読付
研究論文（学術雑誌）, 英語

TOTAL SYNTHESIS OF OPTICALLY-ACTIVE INTEGERRIME, A 12-MEMBERED DILACTONIC PYRROLIZIDINE ALKALOID OF RETRONECINE TYPE .1. ENANTIOSELECTIVE SYNTHESIS OF THE PROTECTED (+/-)-INTEGERRINECIC ACID
H NIWA; Y MIYACHI; Y UOSAKI; K YAMADA
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 27巻, 38号, 掲載ページ 4601-4604, 出版日 1986年, 査読付
研究論文（学術雑誌）, 英語

TOTAL SYNTHESIS OF OPTICALLY-ACTIVE INTEGERRIMINE, A 12-MEMBERED DILACTONIC PYRROLIZIDINE ALKALOID OF RETRONECINE TYPE .2. ENANTIOSELECTIVE SYNTHESIS OF (+)-RETRONECINE
H NIWA; Y MIYACHI; O OKAMOTO; Y UOSAKI; K YAMADA
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 27巻, 38号, 掲載ページ 4605-4608, 出版日 1986年, 査読付
研究論文（学術雑誌）, 英語

TOTAL SYNTHESIS OF OPTICALLY-ACTIVE INTEGERRIMINE, A 12-MEMBERED DILACTONIC PYRROLIZIDINE ALKALOID OF RETRONECINE TYPE .3. REGIOSELECTIVE ELABORATION OF THE UNSYMMETRICAL 12-MEMBERED DILACTONE AND TOTAL SYNTHESIS OF (-)-INTEGERRIMINE
H NIWA; Y MIYACHI; Y UOSAKI; A KURODA; H ISHIWATA; K YAMADA
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 27巻, 38号, 掲載ページ 4609-4610, 出版日 1986年, 査読付
研究論文（学術雑誌）, 英語

STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-TUTIN AND (+)-ASTEROMURIN-A, TOXIC PICROTOXANE SESQUITERPENES
K WAKAMATSU; H KIGOSHI; K NIIYAMA; H NIWA; K YAMADA
TETRAHEDRON, PERGAMON-ELSEVIER SCIENCE LTD, 42巻, 20号, 掲載ページ 5551-5558, 出版日 1986年, 査読付
研究論文（学術雑誌）, 英語

ISOLATION OF PETASITENINE, A CARCINOGENIC PYRROLIZIDINE ALKALOID FROM FARFUGIUM-JAPONICUM
H NIWA; H ISHIWATA; K YAMADA
JOURNAL OF NATURAL PRODUCTS, AMER SOC PHARMACOGNOSY, 48巻, 6号, 掲載ページ 1003-1004, 出版日 1985年11月, 査読付
研究論文（学術雑誌）, 英語

GENOTOXICITY OF PTAQUILOSIDE, A BRACKEN CARCINOGEN, IN THE HEPATOCYTE PRIMARY CULTURE DNA-REPAIR TEST
H MORI; S SUGIE; HIRONO, I; K YAMADA; H NIWA; M OJIKA
MUTATION RESEARCH, ELSEVIER SCIENCE BV, 143巻, 1-2号, 掲載ページ 75-78, 出版日 1985年, 査読付
研究論文（学術雑誌）, 英語

A NEW METHOD FOR DIRECT OXIDATION OF THE METHYLENE GROUP ADJACENT TO A CYCLOPROPANE RING TO THE KETO GROUP
T HASEGAWA; H NIWA; K YAMADA
CHEMISTRY LETTERS, CHEMICAL SOC JAPAN, 14巻, 9号, 掲載ページ 1385-1386, 出版日 1985年, 査読付
研究論文（学術雑誌）, 英語

Total Synthesis of(±)-(Z)-9-(Bromomethylene)-1,5,5-trimethylspiro[5.5]undeca-1,7-dien-3-one, a Brominated Sesquiterpene of Chamigrane Type.
Hideaki Inagaki; Haruki Niwa; Kiyoyuki Yamada
Chemistry Letters, CHEMICAL SOC JAPAN, 14巻, 11号, 掲載ページ 1687-1688, 出版日 1985年, 査読付
研究論文（学術雑誌）, 英語

STUDIES ON PTERIDIUM-AQUILINUM VAR LATIUSCULUM .4. ISOLATION OF 3 PARA-HYDROXYSTYRENE GLYCOSIDES AND AN EFFICIENT METHOD FOR THE ISOLATION OF PTAQUILOSIDE, AN UNSTABLE BRACKEN CARCINOGEN
M OJIKA; H KIGOSHI; H KUYAMA; H NIWA; K YAMADA
JOURNAL OF NATURAL PRODUCTS, AMER SOC PHARMACOGNOSY, 48巻, 4号, 掲載ページ 634-637, 出版日 1985年, 査読付
研究論文（学術雑誌）, 英語

ACTIONS OF PICROTOXININ AND RELATED-COMPOUNDS ON THE FROG SPINAL-CORD - THE ROLE OF A HYDROXYL-GROUP AT THE 6-POSITION IN ANTAGONIZING THE ACTIONS OF AMINO-ACIDS AND PRESYNAPTIC INHIBITION
Y KUDO; H NIWA; A TANAKA; K YAMADA
BRITISH JOURNAL OF PHARMACOLOGY, STOCKTON PRESS, 81巻, 2号, 掲載ページ 373-380, 出版日 1984年, 査読付
研究論文（学術雑誌）, 英語

SEPARATION OF CARCINOGENIC FRACTION OF BRACKEN FERN
HIRONO, I; K YAMADA; H NIWA; Y SHIZURI; M OJIKA; S HOSAKA; T YAMAJI; K WAKAMATSU; H KIGOSHI; K NIIYAMA; Y UOSAKI
CANCER LETTERS, ELSEVIER SCI IRELAND LTD, 21巻, 3号, 掲載ページ 239-246, 出版日 1984年, 査読付
研究論文（学術雑誌）, 英語

ISOLATION AND STRUCTURES OF 2 NEW PARA-HYDROXYSTYRENE GLYCOSIDES, PTELATOSIDE-A AND PTELATOSIDE-B FROM BRACKEN, PTERIDIUM-AQUILINUM VAR LATIUSCULUM, AND SYNTHESIS OF PTELATOSIDE-A
M OJIKA; K WAKAMATSU; H NIWA; K YAMADA; HIRONO, I
CHEMISTRY LETTERS, CHEMICAL SOC JAPAN, 13巻, 3号, 掲載ページ 397-400, 出版日 1984年, 査読付
研究論文（学術雑誌）, 英語

HYPERPLASTIC NODULES OF THE LIVER INDUCED IN RATS FED BRACKEN DIET
HIRONO, I; S AISO; T YAMAJI; H NIWA; M OJIKA; K WAKAMATSU; K YAMADA
CANCER LETTERS, ELSEVIER SCI IRELAND LTD, 22巻, 2号, 掲載ページ 151-155, 出版日 1984年, 査読付
研究論文（学術雑誌）, 英語

Stereocontrolled Total Synthesis of(±)-Hydroxy Patchouli Alcohol and the Corresponding(±)-Carboxylic Acid, Metabolites of Patchouli Akcohol, and(±)-Norpatchoulenol.
Haruki Niwa; Takashi Hasegawa; Norikazu Ban; Kiyoyuki Yamada
Tetrachedron Letters, PERGAMON-ELSEVIER SCIENCE LTD, 25巻, 26号, 掲載ページ 2797-2800, 出版日 1984年, 査読付
研究論文（学術雑誌）, 英語

STEREOCONTROLLED TOTAL SYNTHESIS OF (-)-PICROTOXININ AND (+)-CORIAMYRTIN VIA A COMMON ISOTWISTANE INTERMEDIATE
H NIWA; K WAKAMATSU; T HIDA; K NIIYAMA; H KIGOSHI; M YAMADA; H NAGASE; M SUZUKI; K YAMADA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMER CHEMICAL SOC, 106巻, 16号, 掲載ページ 4547-4552, 出版日 1984年, 査読付
研究論文（学術雑誌）, 英語

STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-TUTIN, A TOXIC SESQUITERPENE OF PICROTOXANE TYPE
K WAKAMATSU; H KIGOSHI; K NIIYAMA; H NIWA; K YAMADA
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 25巻, 35号, 掲載ページ 3873-3874, 出版日 1984年, 査読付
研究論文（学術雑誌）, 英語

STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-ASTEROMURIN-A, A PICROTOXANE SESQUITERPENE ISOLATED FROM THE SCALE INSECT ASTEROCOCCUS-MURATAE KUWANA
K WAKAMATSU; K NIIYAMA; H NIWA; K YAMADA
CHEMISTRY LETTERS, CHEMICAL SOC JAPAN, 13巻, 10号, 掲載ページ 1763-1764, 出版日 1984年, 査読付
研究論文（学術雑誌）, 英語

REPRODUCTION OF ACUTE BRACKEN POISONING IN A CALF WITH PTAQUILOSIDE, A BRACKEN CONSTITUENT
HIRONO, I; Y KONO; K TAKAHASHI; K YAMADA; H NIWA; M OJIKA; H KIGOSHI; K NIIYAMA; Y UOSAKI
VETERINARY RECORD, BRITISH VETERINARY ASSOC, 115巻, 15号, 掲載ページ 375-378, 出版日 1984年, 査読付
研究論文（学術雑誌）, 英語

STRUCTURE AND SYNTHESIS OF MIYAGININ, A PARA-ALLYLPHENYL GLYCOSIDE FROM LESPEDEZA-THUNBERGII FORMA MACRANTHA
M OJIKA; H KUYAMA; H NIWA; K YAMADA
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOC JAPAN, 57巻, 10号, 掲載ページ 2893-2896, 出版日 1984年, 査読付
研究論文（学術雑誌）, 英語

CARCINOGENICITY IN RATS OF PTAQUILOSIDE ISOLATED FROM BRACKEN
HIRONO, I; S AISO; T YAMAJI; H MORI; K YAMADA; H NIWA; M OJIKA; K WAKAMATSU; H KIGOSHI; K NIIYAMA; Y UOSAKI
GANN, JAPAN CANCER ASSN CANCER INST, 75巻, 10号, 掲載ページ 833-836, 出版日 1984年, 査読付
研究論文（学術雑誌）, 英語

STRUCTURE OF PTAQUILOSIDE TETRAACETATE, C28H38O12
S OHBA; Y SAITO; HIRONO, I; H NIWA; M OJIKA; K WAKAMATSU; K YAMADA
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, MUNKSGAARD INT PUBL LTD, 40巻, NOV号, 掲載ページ 1877-1879, 出版日 1984年, 査読付
研究論文（学術雑誌）, 英語

A Convenient Synthesis of(±)-Retronecine.
Haruki Niwa; Akio Kuroda; Kiyoyuki Yamada
Chemistry Letters, CHEMICAL SOC JAPAN, 12巻, 1号, 掲載ページ 125-126, 出版日 1983年, 査読付
研究論文（学術雑誌）, 英語

Total Synthesis of(±)-Cycloseychellene, a Novel Tetracyclic Sesquiterpene.
Haruki Niwa; Norikazu Ban; Kiyoyuki Yamada
Tetrachedron Letters, PERGAMON-ELSEVIER SCIENCE LTD, 24巻, 9号, 掲載ページ 937-938, 出版日 1983年, 査読付
研究論文（学術雑誌）, 英語

SEPARATION AND DETERMINATION OF MACROCYCLIC PYRROLIZIDINE ALKALOIDS OF THE OTONECINE TYPE PRESENT IN THE EDIBLE PLANT PETASITES-JAPONICUS BY REVERSED-PHASE HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY
H NIWA; H ISHIWATA; K YAMADA
JOURNAL OF CHROMATOGRAPHY, ELSEVIER SCIENCE BV, 257巻, 1号, 掲載ページ 146-150, 出版日 1983年, 査読付
研究論文（学術雑誌）, 英語

FARFUGINE, A NEW PYRROLIZIDINE ALKALOID ISOLATED FROM FARFUGIUM-JAPONICUM KITAM
H NIWA; H ISHIWATA; A KURODA; K YAMADA
CHEMISTRY LETTERS, CHEMICAL SOC JAPAN, 12巻, 5号, 掲載ページ 789-790, 出版日 1983年, 査読付
研究論文（学術雑誌）, 英語

PTAQUILOSIDE, A NOVEL NORSESQUITERPENE GLUCOSIDE FROM BRACKEN, PTERIDIUM-AQUILINUM VAR LATIUSCULUM
H NIWA; M OJIKA; K WAKAMATSU; K YAMADA; HIRONO, I; K MATSUSHITA
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 24巻, 38号, 掲載ページ 4117-4120, 出版日 1983年, 査読付
研究論文（学術雑誌）, 英語

STEREOCHEMISTRY OF PTAQUILOSIDE, A NOVEL NORSESQUITERPENE GLUCOSIDE FROM BRACKEN, PTERIDIUM-AQUILINUM VAR LATIUSCULUM
H NIWA; M OJIKA; K WAKAMATSU; K YAMADA; S OHBA; Y SAITO; HIRONO, I; K MATSUSHITA
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 24巻, 48号, 掲載ページ 5371-5372, 出版日 1983年, 査読付
研究論文（学術雑誌）, 英語

Total Synthesis of (±) -Otonecine, a Necine Base of Pyrrolizidine Alkaloids.
Haruki Niwa; Youichi Uosaki; Kiyoyuki Yamada
Tetrachedron Letters, PERGAMON-ELSEVIER SCIENCE LTD, 24巻, 51号, 掲載ページ 5731-5732, 出版日 1983年, 査読付
研究論文（学術雑誌）, 英語

Synthesis of(±)-Carba-Analogs of 5-HPETE and Leukotriene A4, Unstable Intermediates of Slow-Reacting Substance(SRS).
Yoshinobu Arai; Mitoshi Konno; Katsuichi Shimoji; Yoshitaka Konishi; Haruki Niwa; Masaaki Toda; Masaki Hayashi
Chem. Pharm. Bull., PHARMACEUTICAL SOC JAPAN, 30巻, 1号, 掲載ページ 379-382, 出版日 1982年, 査読付
研究論文（学術雑誌）, 英語

STRUCTURAL ANALOGS OF LEUKOTRIENE-C AND LEUKOTRIENE-D AND THEIR CONTRACTILE ACTIVITIES
S OKUYAMA; S MIYAMOTO; K SHIMOJI; Y KONISHI; D FUKUSHIMA; H NIWA; Y ARAI; M TODA; M HAYASHI
CHEMICAL & PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOC JAPAN, 30巻, 7号, 掲載ページ 2453-2462, 出版日 1982年, 査読付
研究論文（学術雑誌）, 英語

ISOLATION AND STRUCTURES OF TRANS-LAURENCENYNE, A POSSIBLE PRECURSOR OF THE C-15 HALOGENATED CYCLIC ETHERS, AND TRANS-NEOLAURENCENYNE FROM LAURENCIA-OKAMURAI
H KIGOSHI; Y SHIZURI; H NIWA; K YAMADA
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 23巻, 14号, 掲載ページ 1475-1476, 出版日 1982年, 査読付
研究論文（学術雑誌）, 英語

Total Synthesis of an Antitumour Antibiotic, (±)-Reductiomycin.
Makoto Ojika; Haruki Niwa; Yoshikazu Shizuri; Kiyoyuki Yamada
J. Chem. Soc., Chem. Commun., ROYAL SOC CHEMISTRY, 11号, 掲載ページ 628-629, 出版日 1982年, 査読付
研究論文（学術雑誌）, 英語

STRUCTURE AND SYNTHESIS OF REDUCTILINE, A NOVEL METABOLITE FROM A VARIANT OF STREPTOMYCES-ORIENTALIS
M OJIKA; Y SHIZURI; H NIWA; K YAMADA; S IWADARE
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 23巻, 47号, 掲載ページ 4977-4980, 出版日 1982年, 査読付
研究論文（学術雑誌）, 英語

(10R, 11R)-(+)-SQUALENE-10, 11-EPOXIDE - ISOLATION FROM LAURENCIA-OKAMURAI AND THE ASYMMETRIC-SYNTHESIS
H KIGOSHI; M OJIKA; Y SHIZURI; H NIWA; K YAMADA
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 23巻, 51号, 掲載ページ 5413-5414, 出版日 1982年, 査読付
研究論文（学術雑誌）, 英語

A CONVENIENT PREPARATION OF N-ACYLPYROGLUTAMIC ACID
K IMAKI; H NIWA; S SAKUYAMA; T OKADA; M TODA; M HAYASHI
CHEMICAL & PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOC JAPAN, 29巻, 9号, 掲載ページ 2699-2701, 出版日 1981年, 査読付
研究論文（学術雑誌）, 英語

A NEW METHOD FOR CLEAVAGE OF ALIPHATIC METHYL ETHERS
H NIWA; T HIDA; K YAMADA
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 22巻, 42号, 掲載ページ 4239-4240, 出版日 1981年, 査読付
研究論文（学術雑誌）, 英語

LAURENCENYNE, A PLAUSIBLE PRECURSOR OF VARIOUS NON-TERPENOID C-15-COMPOUNDS, AND NEOLAURENCENYNE FROM THE RED ALGA LAURENCIA-OKAMURAI
H KIGOSHI; Y SHIZURI; H NIWA; K YAMADA
TETRAHEDRON LETTERS, PERGAMON-ELSEVIER SCIENCE LTD, 22巻, 47号, 掲載ページ 4729-4732, 出版日 1981年, 査読付
研究論文（学術雑誌）, 英語

Recent Studies on the Chemical Synthesis of Eicosanoids.
E. J. Corey; H. Niwa; J. R. Falck; C. Mioskowski; Y. Arai; A. Marfat
"Advances in Prostaglandin and Thromboxane Research" ed. by B. Samuelsson, P. W. Ramwell, and R. Paoletti, Raven Press, New York, 6巻, 掲載ページ 19-25, 出版日 1980年, 査読付
研究論文（学術雑誌）, 英語

Synthesis of 15,17-Methylene-prostaglandins.
Haruki Niwa; Masayasu Kurono
Chemistry Letters, 8巻, 1号, 掲載ページ 23-26, 出版日 1979年, 査読付
研究論文（学術雑誌）, 英語

Synthesis of a New Prostaglandin Endoperoxide (PG H2) Analog and Its Function as an Inhibitor of the Biosynthesis of Thromboxane A2 (TX A2).
E. J. Corey; Haruki Niwa; Miriam Bloom; Peter W. Ramwell
Tetrachedron Letters, 8号, 掲載ページ 671-674, 出版日 1979年, 査読付
研究論文（学術雑誌）, 英語

Selective Epoxidation of Eicosa-cis-5,8,11,14-tetraenoic(Arachidonic)Acid and Eicosa-cis-8,11,14-trienoic Acid.
E. J. Corey; Haruki Niwa; J. R. Falck
J. Am. Chem. Soc., 101巻, 6号, 掲載ページ 1586-1587, 出版日 1979年, 査読付
研究論文（学術雑誌）, 英語

Total Synthesis of (S)-12 Hydroxy-5,8,14-cis-10-trans-eicosatetraenoic Acid(Samuelsson's HETE).
E. J. Corey; Haruki Niwa; Jochen Knolle
J. Am. Chem. Soc., 100巻, 6号, 掲載ページ 1942-1943, 出版日 1978年, 査読付
研究論文（学術雑誌）, 英語

Synthesis of 15,19-Methano-ω-nor-prostaglandins.
Haruki Niwa; Masayasu Kurono
Chemistry Letters, 6巻, 10号, 掲載ページ 1211-1214, 出版日 1977年, 査読付
研究論文（学術雑誌）, 英語

The Alkaloids from the Fruits of the Plant Daphniphyllaceae.
Masaaki Toda; Haruki Niwa; Hajime Irikawa; Yoshimasa Hirata; Shosuke Yamamura
Tetrahedron, 30巻, 16号, 掲載ページ 2683-2688, 出版日 1974年, 査読付
研究論文（学術雑誌）, 英語

Chemical Studies on Nitrogen Heterocylic Skeleton of the Daphniphyllum Alkaloids.
Haruki Niwa; Masaaki Toda; Sueaki Ishimaru; Yoshimasa Hirata; Shosuke Yamamura
Tetrahedron, 30巻, 17号, 掲載ページ 3031-3036, 出版日 1974年, 査読付
研究論文（学術雑誌）, 英語

The Structure of Daphniphyllidine.
Masaaki Toda; Haruki Niwa; Yoshimasa Hirata; Shosuke Yamamura
Tetrachedron Letters, 14巻, 11号, 掲載ページ 797-798, 出版日 1973年, 査読付
研究論文（学術雑誌）, 英語

Biosynthesis of Daphniphyllum Alkaloids.
Kazuo T. Suzuki; Shigenobu Okuda; Haruki Niwa; Masaaki Toda; Yoshimasa Hirata; Shosuke Yamamura
Tetrachedron Letters, 14巻, 11号, 掲載ページ 799-802, 出版日 1973年, 査読付
研究論文（学術雑誌）, 英語

Biosynthesis of Daphnilactone-B.
Haruki Niwa; Yoshimasa Hirata; Kazuo T. Suzuki; Shosuke Yamamura
Tetrachedron Letters, 14巻, 23号, 掲載ページ 2129-2132, 出版日 1973年, 査読付
研究論文（学術雑誌）, 英語

2-Azabicyclo[3.3.1]non-1-ene Systems as Reaction Intermediates.
Masaaki Toda; Haruki Niwa; Kazuharu Ienaga; Yoshimasa Hirata; Shosuke Yamamura
Tetrachedron Letters, 13巻, 5号, 掲載ページ 335-338, 出版日 1972年, 査読付
研究論文（学術雑誌）, 英語

Daphnilactone-B, a Major Alkaloid, from the Fruits of Daphniphyllaceae.
Haruki Niwa; Masaaki Toda; Yoshimasa Hirata; Shosuke Yamamura
Tetrachedron Letters, 13巻, 26号, 掲載ページ 2697-2700, 出版日 1972年, 査読付
研究論文（学術雑誌）, 英語

生物発光の原理と応用
丹羽治樹
出版日 2012年07月, 自動車技術会 関東支部報「高翔」, 58号, 掲載ページ xx, 日本語, 記事・総説・解説・論説等（その他）

生物発光の原理と応用
丹羽治樹
出版日 2012年04月, 日本大気電気学会誌, 6巻, 1号, 掲載ページ 31-34, 日本語, 記事・総説・解説・論説等（その他）

オワンクラゲの生物発光機構
丹羽治樹
出版日 2009年04月, 岩波書店「科学」, 79巻, 4号, 掲載ページ 96-97, 日本語, 記事・総説・解説・論説等（その他）

生物はなぜ光るのか－生物発光とその応用－
丹羽治樹
出版日 2005年10月, ２００５第１９回「大学と科学」公開シンポジウム講演収録集 『不思議な生物現象の化学』, 掲載ページ pp. 171-182, 日本語, 記事・総説・解説・論説等（その他）

発光巻貝ラチアの発光機構研究:ラチアルシフェリンアナログのK_mと発光反応生成物の分析
正木美津希; 間蓑雅; 永家聖; 中村光裕; 小島哲; 近江谷克裕; 牧昌次郎; 平野誉; 丹羽治樹
出版日 2005年03月11日, 日本化学会講演予稿集, 85th巻, 2号, 掲載ページ 862, 日本語, 0285-7626, 200902221179445784

生物発光のメカニズムとその応用
丹羽治樹
出版日 2002年, 現代化学, 379号, 掲載ページ 29-36, 日本語, 記事・総説・解説・論説等（その他）

有機合成における電極反応の応用（共著）
牧昌次郎; 丹羽治樹
The chemical, site-specific oxidations of saturated hydrocarbons as mimic for biological process are important subjects in synthetic organic chemistry. Such oxidations are seldom achieved in conventional chemistry. The development of such methodology is challenging, extensive studies which are currently ongoing in many laboratories. Recently we found that the electrochemical oxidation can achieve the site-specific hydroxylation of a certain inactivated methine and methylene groups in moderate or good yields. Further we achieved stereoselective chlorination of steroidal double bonds and selective cleavage of styrylic olefins as well as the triene of Vitamin D-2 by electrolysis. Descried herein are the scope and limitation, and the synthetic application of such electrochemical oxidation reactions., SOC SYNTHETIC ORGANIC CHEM JPN, 出版日 1998年09月, 有機合成化学協会誌, 56巻, 9号, 掲載ページ 725-735, 日本語, 査読付, 記事・総説・解説・論説等（その他）, 0037-9980, WOS:000076044300003

絵で見るバイオ;オワンクラゲの増感生物発光機構
丹羽治樹
出版日 1998年, バイオサイエンスとインダストリー, 56巻, 7号, 掲載ページ 443, 日本語, 記事・総説・解説・論説等（その他）

トピックス:オワンクラゲの増感生物発光機構
丹羽治樹
出版日 1998年, バイオサイエンスとインダストリー, 56巻, 7号, 掲載ページ 471-472, 日本語, 記事・総説・解説・論説等（その他）

発光反応(特集・光る生物-ホタルを中心に).
丹羽治樹
裳華房, 出版日 1996年, 遺伝, 50巻, 11号, 掲載ページ 35-42, 日本語, 記事・総説・解説・論説等（その他）, 0387-0022, 40000132708, AN00015468

植物神経毒アニサチンの合成
丹羽治樹; 山田靜之
出版日 1991年, ファルマシア(日本薬学会), 27巻, 7号, 掲載ページ 924-927, 日本語, 記事・総説・解説・論説等（その他）

植物起源の発がん物質の合成
山田靜之; 丹羽治樹; 木越英夫
出版日 1990年, 化学増刊118「生体機能解明のための化学合成」 化学同人(京都), 掲載ページ 191-201, 日本語, 記事・総説・解説・論説等（その他）

多官能性天然生理活性物質の全合成.大環状ピロリチジンアルカロイドの全合成
丹羽治樹
SOC SYNTHETIC ORGANIC CHEM JPN, 出版日 1988年07月, 有機合成化学協会誌, 46巻, 7号, 掲載ページ 693-703, 日本語, 記事・総説・解説・論説等（その他）, 0037-9980, WOS:A1988P301900006

ピクロトキサン型セスキテルペノイドの全合成
丹羽治樹; 山田静之
出版日 1986年, 有機合成化学協会誌, 44巻, 3号, 掲載ページ 180-190, 日本語, 記事・総説・解説・論説等（その他）

医学のための細胞生物学：コラム「ＧＦＰと下村脩先生」
丹羽治樹; コラム執筆分担; 監修 永田和宏; 田浩平
日本語, 共著, 南山堂, 出版日 2009年08月

岩波：科学 Vol. 71, No. 4 (2009).特集「クラゲ」-オワンクラゲの生物発光機構-
丹羽治樹
日本語, 共著, クラゲの生物発光, 岩波書店, 出版日 2009年04月

天然物化学ー 海洋生物編： 1.2.7「海洋生物の発光現象」
丹羽治樹; 執筆分担; 監修 山村庄助; 長谷川宏司
日本語, 共著, 1.2.7「海洋生物の発光現象, アイピーシー, 出版日 2008年06月

生物物理学ハンドブック： 7.6 生物発光
丹羽治樹
日本語, 共著, 7.6 生物発光, 朝倉書店, 出版日 2007年04月

別冊『化学：分子イメージング最前線』 1.4 入門「自然界に光る生き物とその原理」
丹羽治樹
日本語, 共著, 1.4：入門「自然会の”光る生物”とその原理」, 化学同人, 出版日 2007年04月

天然物化学ー植物編
丹羽治樹; 執筆分担; 監修 山村庄助; 長谷川宏司
日本語, 共著, 第３章 植物由来の生理活性天然有機化合物の合成 3.1.2 プタキロシン、アニサチン, アイピーシー, 出版日 2007年02月

バイオサイエンス化学－生命から学ぶ化学－ 第４章 生命の物質－炭素化合物
新井孝夫; 大森大二郎; 立屋敷哲; 丹羽治樹
日本語, 共著, 第４章 生命の物質－炭素化合物, 東京化学同人, 出版日 2003年03月

有機化学実験のてびき-3
丹羽治樹; 執筆分担; 監修 後藤俊夫; 芝 哲夫; 浦輝夫
日本語, 共著, 化学同人, 出版日 1990年

有機化学実験のてびき-4
丹羽治樹; 執筆分担; 監修 後藤俊夫; 芝 哲夫; 浦輝夫
日本語, 共著, 化学同人, 出版日 1990年

有機化学実験のてびき-1
丹羽治樹; 執筆分担; 監修 後藤俊夫; 芝 哲夫; 浦輝夫
日本語, 共著, 化学同人, 出版日 1988年

生物発光、温故知新
丹羽治樹
口頭発表（招待・特別）, 日本語, 生物発光化学発光研究会第30学術講演会（東工大大岡山キャンパス, 目黒区）、抄録集PLxx（2013.11.02), 生物発光化学発光研究会第30学術講演会（東工大大岡山キャンパス, 目黒区）、抄録集PLxx（2013.11.02)
発表日 2013年11月

ホタル生物発光系をモデルとした人工発光系の創製と実用化
岩野 智; 伊藤 和人; 北田 昇雄; 牧 昌次郎; 丹羽 治樹
その他, 日本語, 第8回産学官連携DAY in 電通大 電気通信大学 産学官連携センター産学連携支援部門第１７回共同研究成果発表会(電気通信大学、調布）（2012.6.6), 第8回産学官連携DAY in 電通大 電気通信大学 産学官連携センター産学連携支援部門第１７回共同研究成果発表会(電気通信大学、調布）（2012.6.6)
発表日 2012年06月

生物発光の化学とその イメージングへの応用
丹羽治樹
口頭発表（基調）, 日本語, 平成19年度日本バイオイメージング学会公開講座 「理学と工学が拓くバイオイメージング」 (2007.10.31、東京理科大学野田キャンパス）, 平成19年度日本バイオイメージング学会公開講座 「理学と工学が拓くバイオイメージング」 (2007.10.31、東京理科大学野田キャンパス）, 国内会議
発表日 2007年10月

生物発光研究の新展開：ラチア、ホタル、発光ゴカイ
丹羽治樹
口頭発表（招待・特別）, 日本語, 第八回神奈川ハイテク・リサーチ・センター研究発表会 (神奈川大学、2006.6.10), 第八回神奈川ハイテク・リサーチ・センター研究発表会 (神奈川大学、2006.6.10)
発表日 2006年06月

ホタルの光～生物の光通信～
丹羽治樹
口頭発表（基調）, 日本語, 『夏休み子供のための公開シンポジウム：生物の情報通信を探る』（平成１７年度文部科学省「科学研究補助金研究成果公開促進費」補助事業）補助資料(2005.8.9), 国内会議
発表日 2005年08月

生物はなぜ光るのか－生物発光とその応用－
丹羽治樹
口頭発表（基調）, 日本語, 第１９回「大学と科学」公開シンポジウム 『不思議な生物現象の化学』, 第１９回「大学と科学」公開シンポジウム 『不思議な生物現象の化学』(2005.1.29), 国内会議
発表日 2005年01月

Targetted Pursuit of Challenging Bioactive Molecules [Summary Report of Research Projekt (1999~2002)]
Haruki Niwa
その他, 英語, The Grant-in-Aid for Scientific Research on Priority Areas; The Ministry of Education, Culture, Sports, Scinece and Technology
発表日 2004年04月

巻き貝ラチア生物発光の分子機構
丹羽治樹
口頭発表（招待・特別）, 日本語, 日本化学会第80秋季年会（千葉,千葉）,講演予稿集，(2001.9.21)，（招待）
発表日 2001年09月

生物と光―生物発光の分子基盤研究とその応用
丹羽治樹
口頭発表（招待・特別）, 日本語, 第38回茅コンファランス「光科学の新しい展開とその応用」（福島，裏磐梯）
発表日 2000年11月

発光クラゲの緑色蛍光蛋白質（ＧＦＰ）の化学
丹羽治樹
口頭発表（招待・特別）, 日本語, 第１１回海洋生物活性 談話会（厚岸）（１９９７．５．２５）
発表日 1997年05月

有機化学2
東邦大学大学院理学研究科

有機化学2
東邦大学大学院理学研究科

有機化学2
東邦大学大学院理学研究科

日本化学会

生物発光・化学発光研究会

検出装置、検出方法、及び検出器
特許権, 山田幸夫, 西村吾朗, 丹羽治樹, 牧昌次郎, 道脇幸博, 小池卓二, 鈴木崇弘, 田代剛大, 特願2020-123183(優先権主張番号:特願2019-132298 出願日2019.7.17), 出願日: 2020年07月17日, 電気通信大学、北海道大学、昭和大学, 特開2021-16798, 公開日: 2021年02月15日, 国内

特願2014-189314 新規複素環式化合物及びその塩、並びに、発光基質組成物(原特願2013-198998; 2013/9/25)
特許権, 牧 昌次郎, 丹羽治樹, 特願2014-189314(原特願2013-198998; 2013/9/25), 出願日: 2014年09月17日, 電気通信大学, 特開2015-193584, 公開日: 2015年11月05日, 特許第6353751, 発行日: 2018年06月15日

特願2013-530040：ルシフェラーゼの発光基質
特許権, 西山 繁, 齋藤 毅, 牧 昌次郎, 丹羽治樹, 特願2013-530040, 出願日: 2012年08月22日, 国立大学法人 電気通信大学, WO/2013/027770 A1, 公開日: 2013年02月28日, 特許第6049019, 発行日: 2016年12月02日

特願2013-097755 新規ハロゲン化水素塩
特許権, 牧 昌次郎, 丹羽治樹, 特願2013-097755, 出願日: 2013年05月07日, 国立大学法人電気通信大学, 特開2014-218456, 公開日: 2014年11月20日, 特許第6011974号, 発行日: 2016年09月30日

PCT/JP2012/071207 (特願2011-182224) Int. Appl.Luciferin analog and its use for luminescent substrate for luciferase and luminescence detection kit
特許権, Nishiyama, Shigeru, Saito, Tsuyoshi, Maki, Shojiro, Niwa, Haruk, PCT/JP2012/071207, 出願日: 2012年08月22日,  The University of Electro-Communications, Japan, CN103796999A, 公開日: 2014年05月14日, ZL201280041269.3, 発行日: 2015年07月22日

特願2010-137031 遷移元素触媒およびその製造方法、並びに選択的水素添加方法
特許権, 牧昌次郎, 丹羽治樹, 特願2010-137031, 出願日: 2010年06月16日, 国立大学法人電気通信大学, 特開2011-020116, 公開日: 2011年02月03日, 特許第5605619, 発行日: 2014年09月05日

PCT/JP2012/071207 (特願2011-182224) Int. Appl.Luciferin analog and its use for luminescent substrate for luciferase and luminescence detection kit
特許権, Nishiyama, Shigeru, Saito, Tsuyoshi, Maki, Shojiro, Niwa, Haruk, PCT/JP2012/071207, 出願日: 2012年08月22日,  The University of Electro-Communications, Japan, US2014-0221665A1, 公開日: 2014年08月07日

PCT/JP2012/071207 (特願2011-182224) Int. Appl.Luciferin analog and its use for luminescent substrate for luciferase and luminescence detection kit
特許権, Nishiyama, Shigeru, Saito, Tsuyoshi, Maki, Shojiro, Niwa, Haruk, PCT/JP2012/071207, 出願日: 2012年08月22日,  The University of Electro-Communications, Japan, EP2754657A1, 公開日: 2014年07月16日

特願2012-265382 環化化合物の製造方法、及び、環化化合物を含有する溶液の発光方法
特許権, 斎藤 毅, 西山 繁, 井岡秀二, 牧 昌次郎, 丹羽治樹, 特願2012-265382, 出願日: 2012年12月04日, 学校法人慶応義塾、国立大学法人電気通信大学, 特開2014-108957, 公開日: 2014年06月12日

特願2009-064595：波長が制御されたルシフェラーゼの発光基質および製造方法
特許権, 牧 昌次郎, 小島 哲, 丹羽治樹, 特願2009-064595, 出願日: 2009年03月17日, 電気通信大学, 特開2010-215795, 公開日: 2010年09月30日, 特許第5550035号, 発行日: 2014年05月30日

特願2008-023396:「ルシフェラーゼの発光基質」
特許権, 牧 昌次郎, 小島 哲, 丹羽 治樹, 特願2008-023396, 出願日: 2008年02月02日, 国立大学法人電気通信大学, 特開2009-184932, 公開日: 2009年08月20日, 特許第5464311, 発行日: 2014年01月31日

特願2012-049619：ルシフェラーゼの発光基質
特許権, 牧 昌次郎, 丹羽 治樹, 特願2012-49619, 出願日: 2012年03月06日, 国立大学法人 電気通信大学, 特開2013-184909, 公開日: 2013年09月19日

PCT/JP2012/071207 (特願2011-182224) Int. Appl.Luciferin analog and its use for luminescent substrate for luciferase and luminescence detection kit
特許権, Nishiyama, Shigeru, Saito, Tsuyoshi, Maki, Shojiro, Niwa, Haruk, PCT/JP2012/071207, 出願日: 2012年08月22日,  The University of Electro-Communications, Japan, WO/2013/027770 A1, 公開日: 2013年02月28日

PCT/JP2007/056227（特願2008-509744）:複素環化合物及び発光方法
特許権, 牧 昌次郎, 小島 哲, 丹羽治樹, 平野 誉, PCT/JP2007/056227, 出願日: 2007年03月26日, 電気通信大学, WO2007/116687, 公開日: 2007年10月18日, 特許第5194258号, 発行日: 2013年02月15日

特願2011-108654 蛍光色素
特許権, 平野 誉, 中川 達規, 牧 昌次郎, 丹羽治樹, 特願2011-108654, 出願日: 2011年05月13日, 国立大学法人 電気通信大学, 特開2012-241014, 公開日: 2012年12月10日

（取下げ擬制）特願2011-182224：ルシフェラーゼの発光基質
特許権, 西山 繁, 齋藤 毅, 牧 昌次郎, 丹羽治樹, (取下げ擬制)特願2011-182224, 出願日: 2011年08月24日, 国立大学法人 電気通信大学

特願2009-187979：抗体－ルシフェリルペプチド複合体、これを用いた被検物質の測定方法及び被検物質の測定試薬並びに測定試薬の調製方法
特許権, 志賀 一樹, 河口 成, 牧 昌次郎, 丹羽 治樹, 特願2009-187979, 出願日: 2009年08月14日, キッコーマン株式会社、国立大学法人電気通信大学、株式会社キャンパスクリエイト, 特開2011-037791, 公開日: 2011年02月24日

特願2004-379971：天然型L-システインまたはその誘導体を用いたホタル発光基質の生合成システム及び本システムを含んだ発光基質溶液
特許権, 近江谷克裕, 丹羽一樹, 丹羽治樹, 中村光裕, 龍福正行, 特願2004-379971, 出願日: 2004年12月28日, 産業技術総合研究所、電気通信大学、東洋ビーネット, 特開2006-180825, 公開日: 2006年07月13日, 特許4682310, 発行日: 2011年02月18日

PCT/JP2009/000376：ルシフェラーゼの発光基質
特許権, 牧 昌次郎, 小島 哲, 丹羽治樹, PCT/JP2009/000376, 出願日: 2009年02月02日, 電気通信大学, キャンパスクリエイト, US2011/033878A1, 公開日: 2011年02月10日

PCT/JP2010/053177波長が制御されたルシフェラーゼの発光基質および製造方法
特許権, 牧,小島,丹羽, PCT/JP2010/053177, 出願日: 2010年02月28日, 電気通信大学、キャンパスクリエイト, WO/2010/106896 A1, 公開日: 2010年09月23日

特願2009-027654 ルシフェラーゼの発光基質
特許権, 牧 昌次郎, 小島 哲, 丹羽治樹, 特願2009-027654, 出願日: 2009年02月09日, 電気通信大学, 特開2010-180191, 公開日: 2010年08月19日

特願2004-067098: イミダゾピラジノン誘導体及びビスアミノピラジノン誘導体並びに化学発光物質
特許権, 特願2004-067098, 出願日: 2004年03月10日, 三菱科学(株), 特開2005-255579, 公開日: 2005年09月22日, 特許4561132, 発行日: 2010年08月06日

特願2008-244890［アシルアミノピラジナート-O,N］ーボロン誘導体および蛍光色素
特許権, 平野 誉, 牧 昌次郎, 丹羽治樹, 特願2008-244890, 出願日: 2008年09月24日, 電気通信大学, 特開2010-077040, 公開日: 2010年04月08日

特願2008-192596: ε-N-ルシフェリルリシン化合物、これを用いたペプチド標識剤及びペプチド標識方法
特許権, 牧 昌次郎, 小島 哲, 丹羽 治樹, 河口 成, 特願2008-192596, 出願日: 2008年07月25日, 電気通信大学、キッコーマン株式会社、株式会社キャンパスクリエイト, 特開2010-30918, 公開日: 2010年02月12日

特願2003-195905: ビスイミダゾピラジノン系新規蛍光性・化学発光生物質
特許権, 平野 誉, 丹羽治樹, 牧 昌次郎, 特願2003-195905:, 出願日: 2003年07月11日, 三菱化学, 特開2005-29500, 公開日: 2005年02月03日, 特許4363098, 発行日: 2009年08月28日

特願2003-026134: 還元触媒及びその製造方法、並びに選択的水素添加方法
特許権, 牧 昌次郎, 丹羽治樹, 特願2003-026134, 出願日: 2003年02月02日, 独立行政法人科学技術振興機構, 特開2004-23714, 公開日: 2004年08月26日, 特許4116891, 発行日: 2008年04月25日

特願2006-086175:複素環化合物及び発光方法
特許権, 牧 昌次郎, 小島 哲, 丹羽治樹, 平野 誉, 特願2006-086175, 出願日: 2006年03月27日, 電気通信大学, 特開2007-194258, 公開日: 2007年08月02日

特願2002-33258: パラジウム触媒を用いた選択的水素添加反応方法
特許権, 牧 昌次郎, 丹羽治樹, 佐野淳典, 特願2002-33258, 出願日: 2002年02月08日, 和光純薬工業 (株), 特開2003-238482, 公開日: 2003年08月27日, 特許第3976579, 発行日: 2007年06月29日

特願2005-031574:複素環化合物及び発光甲虫ルシフェラーゼ発光系用発光物質
特許権, 丹羽治樹, 牧昌次郎, 平野 誉, 特願2005-031574, 出願日: 2005年02月08日, 電気通信大学, 特開2006-219381, 公開日: 2006年08月24日

PCT/JP2005/23847：天然型L-システインまたはその誘導体を用いたホタル発光基質の生合成システム及び本システムを含んだ発光基質溶液
特許権, 近江谷克裕, 丹羽一樹, 丹羽治樹, 中村光裕, 龍福正行, PCT/JP2005/023847, 出願日: 2005年12月27日, 産業技術総合研究所、電気通信大学、東洋ビーネット, WO/2006/070775, 公開日: 2006年07月06日

特願2003-292606: 発光キノコヤコウタケの簡便栽培法
特許権, 杉本正志, 丹羽治樹, 特願2003-292606, 出願日: 2003年07月09日, 杉本正志, 特開2005-27634, 公開日: 2005年02月03日

特願2003-116616: 芳香族有機化合物の分解方法
特許権, 牧昌次郎, 丹羽治樹, 平野 誉, 特願2003-116616, 出願日: 2003年04月22日, 独立行政法人 科学技術振興機構, 特開2004-321275, 公開日: 2004年11月18日

特願2002-80931: 新規なパラジウム触媒
特許権, 牧昌次郎, 丹羽治樹, 佐野淳典, 大野桂二, 特願2002-80931, 出願日: 2002年03月22日, 和光純薬工業 (株)., 特開2003-275593, 公開日: 2003年09月30日

特願2002-80930: パラジウムブラックの新規な製造方法
特許権, 牧 昌次郎, 丹羽 治樹, 佐野 淳典, 大野 桂二, 特願2002-80930, 出願日: 2002年03月22日, 和光純薬工業 (株), 特開2003-275586, 公開日: 2003年09月30日

特願2002-80929: 担持型パラジウム触媒
特許権, 牧昌次郎, 丹羽治樹, 佐野淳典, 大野桂二, 特願2002-80929, 出願日: 2002年03月22日, 和光純薬工業 (株)., 特開2003-275585, 公開日: 2003年09月30日

特願2000-340644: アルケン類の選択的水素添加反応並びにこれに用いる触媒及び触媒構造体
特許権, 小泉 恵, 錦 善則, 古田 常人, 丹羽 治樹, 牧 昌次郎, 特願2000-340644, 出願日: 2000年11月08日, ペルメレック電極 (株)., 特開2002-145818, 公開日: 2002年05月22日

特願2000-133584: アルケン類の選択的水素添加方法
特許権, 小泉 恵, 尾形節郎, 錦 善則, 井上博史, 岩倉千秋, 丹羽治樹, 牧昌次郎, 特願2000-133584, 出願日: 2000年05月02日, ペルメレック電極 (株), 特開2001-316315, 公開日: 2001年11月13日

特願平11-137401: アルケンの選択的水素添加方法
特許権, 吉田泰樹, 尾形節郎, 井上博史, 岩倉千秋, 丹羽治樹, 牧昌次郎, 特願平11-137401, 出願日: 1999年05月18日, ペルメレック電極 (株), 特開2000-328278, 公開日: 2000年11月28日

特開昭52-91847: プロスタグランジン関連化合物
特許権, 小野薬品工, 特願昭52-4888, 出願日: 1977年01月21日, 特開昭52-91847, 公開日: 1977年08月02日

特開昭52-77027: 2－(4－イソブチルフェニル)プロピオン酸
特許権, 黒野昌庸, 戸田正明, 丹羽治樹, 特願昭50-151984, 出願日: 1975年12月22日, 小野薬品工業株式会社, 特開昭52-77027, 公開日: 1977年06月29日

特開昭52-62237: α置換フェニル・アルカン・カルボン酸の製造法
特許権, 黒野昌庸, 戸田正明, 丹羽治樹, 小菅俊士, 飯田貴史, 成田研一, 特願昭50-138041, 出願日: 1975年11月19日, 小野薬品工業(株), 特開昭52-62237, 公開日: 1977年05月23日

特開昭52-53833: α置換フェニル・アルカン・カルボン酸の製造法
特許権, 黒野昌庸, 戸田正明, 丹羽治樹, 特願昭50-128906, 出願日: 1975年10月28日, 小野薬品工業(株), 特開昭52-53833, 公開日: 1977年04月30日

特開昭51-86447: 1β，5β－2－オキサ－3－ヒドロキシ－6β－置換メチル－7α－置換オキシ－ビシクロ［3.3.0］オクタン類の製造法
特許権, 黒野昌庸, 丹羽治樹, 特願昭50-9884, 出願日: 1975年01月24日, 小野薬品工業(株)., 特開昭51-86447, 公開日: 1976年07月29日