論文 - 山村 初雄
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Preparation of Amylose‐Mimicking Polymers for the Purification of Maltose‐Binding Protein
Atsushi Miyagawa, Nami Yamamoto, Hatsuo Yamamura
Journal of Polymer Science 2025年02月
掲載種別：研究論文（学術雑誌） 出版者・発行元：Wiley
ABSTRACT
Maltose‐binding protein (MBP) is used as affinity tags for purifying recombinant proteins via amylose affinity gels. However, the gel often yields a low quantity of the purified protein due to the biodegradability and low water solubility of immobilized amylose. Herein, water‐soluble, anti‐biodegradation amylose‐mimicking polymers are synthesized by polymerizing a maltose monomer with a norbornene group, then copolymerizing it with a glucose monomer and norbornene. The synthesized polymers are further modified via hydrogenation and hydroxylation to alter their properties. The binding affinities of these polymers, which are evaluated using a quartz crystal microbalance instrument, indicated their binding to MBP mimics that of amylose. Furthermore, the polymer is immobilized on an agarose gel to prepare an affinity gel for MBP, which absorbs concanavalin A and MBP before eluting them. However, only 15% of MBP is absorbed, with the majority passing through the gel. This indicates that maltose is short enough to efficiently absorb MBP. However, amylose‐mimicking polymers have higher water solubilities and are easier to handle than amylose polymers, making them expected to exhibit a higher MBP absorbability. Hence, optimizing ligand length and structure is key to improving MBP binding. Further, designs should focus on enhancing stability and binding efficiency to improve affinity purification.DOI： 10.1002/pol.20241130
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Amphiphilic cyclodextrin derivatives with antibacterial activity: chemical mutation and structure-activity relationship 査読あり
Hatsuo Yamamura, Ayame Kato, Eri Yamada, Hisato Kato, Takashi Katsu, Kazufumi Masuda, Kayo Osawa, and Atsushi Miyagawa
New Journal of Chemistry 48 12355 - 12361 2024年07月
担当区分：筆頭著者, 責任著者 記述言語：英語 掲載種別：研究論文（学術雑誌）
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安全で抗菌性に優れた新規オリゴ糖誘導体—防腐効果のある化粧品原料の開発— 査読あり
小見宏幸，髙田健太，竹内彩乃，村上栞菜，宮川 淳，山村初雄
日本香粧品学会誌 48 ( 2 ) 82 - 88 2024年06月
担当区分：最終著者, 責任著者 記述言語：日本語 掲載種別：研究論文（学術雑誌）
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One-step synthesis of sugar nucleotides under optimized conditions 査読あり
Kota Fujihara, Hatsuo Yamamura and Atsushi Miyagawa
Synthetic communications 54 ( 15 ) 1245 - 1251 2024年05月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Facile synthesis of β-1,3-glucan disaccharides using acyl protected glycosyl donors and acceptors prepared from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 招待あり 査読あり
Atsushi Miyagawa, Ryusuke Tomita, Hatsuo Yamamura
24 ( 10 ) 69 - 78 2024年05月
担当区分：最終著者 記述言語：英語
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Atsushi Miyagawa, Nami Yamamoto, Ayane Ohno, Hatsuo Yamamura
International Journal of Biological Macromolecules 264 130546 2024年03月
担当区分：最終著者 記述言語：英語 掲載種別：研究論文（学術雑誌）
その他リンク： https://www.sciencedirect.com/science/article/abs/pii/S0141813024013497
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Synthesis of cyclodextrin dimers via Diels–Alder reaction 査読あり
A. Miyagawa , T. Hasegawa, H. Yamamura
Synthetic Ccmmunications 53 ( 22 ) 1878 - 1885 2023年10月
担当区分：最終著者 記述言語：英語 掲載種別：研究論文（学術雑誌）
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Anti-bacterial ß-cyclodextrin derivatives inspired by the anti-microbial peptide polymyxin in order to better understand the role of single hydrophobic chain tail in selective anti-bacterial activity 査読あり
New Journal of Chemistry 47 10921 - 10929 2023年04月
担当区分：筆頭著者, 責任著者 記述言語：英語 掲載種別：研究論文（学術雑誌）
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Identification of a tomato UDP-arabinosyltransferase for airborne volatile reception 査読あり
K. Sugimoto, E. Ono, T. Inaba, T. Tsukahara, K. Matsui, M. Horikawa, H. Toyonaga, K. Fujikawa, T. Osawa, S. Homma, Y. Kiriiwa, Ippei Ohmura, Atsushi Miyagawa, Hatsuo Yamamura, M. Fujii, R. Ozawa, B.Watanabe, K. Miura, H. Ezura, T. Ohnishi, J. Takabayashi
Nature Communications 14 677 2023年02月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Synthesis of antimicrobial polymers with mannose residues for binding to the FimH adhesin of Escherichia coli 査読あり
Atsushi Miyagawa, Shinya Ohno, Hatsuo Yamamura
Journal of Polymer Science 2022年12月
担当区分：最終著者 記述言語：英語
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UDP glucose, cereblon dependent proinsulin degrader 査読あり
Cho, J.; Miyagawa, A.; Yamaguchi, K.; Abe, W.; Tsugawa, Y.; Yamamura, H.; Imai, T.
Scientific Reports 11 24516 2022年08月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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UDP-glucose: A cereblon-dependent glucokinase Protein Degrader 査読あり
Cho, J.; Miyagawa, A.; Yamaguchi, K.; Abe, W.; Tsugawa, Y.; Yamamura, H.; Imai, T.
Int. J. Mol. Sci. 23 9094 2022年04月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Antimicrobial activities of amphiphilic cationic polymers and their efficacy of combination with novobiocin 査読あり
Miyagawa, A., Ohno, S., Hattori, T., Yamamura, H.
Journal of Biomaterials Science, Polymer Edition 22 299 - 312 2022年02月
担当区分：最終著者 掲載種別：研究論文（学術雑誌）
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Antibacterial Activity of Membrane-Permeabilizing Bactericidal Cyclodextrin Derivatives 査読あり
Hatsuo Yamamura, Tatsuya Hagiwara, Yuma Hayashi, Kayo Osawa, Hisato Kato, Takashi Katsu, Kazufumi Masuda, Ayumi Sumino, Hayato Yamashita, Ryo Jinno, Masayuki Abe, Atsushi Miyagawa
ACS Omega 6 ( 47 ) 31831 - 31842 2021年11月
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Antibacterial Activity of Membrane-permeabilizing Bactericidal Cyclodextrin Derivatives 査読あり 国際誌
Hatsuo Yamamura, Tatsuya Hagiwara, Yuma Hayashi, Kayo Osawa, Hisato Kato, Takashi Katsu, Kazufumi Masuda, Ayumi Sumino, Hayato Yamashita, Ryo Jinno, Masayuki Abe, Atsushi Miyagawa
ACS Omega 2021年11月
担当区分：筆頭著者 記述言語：英語 掲載種別：研究論文（学術雑誌）
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Antimicrobial activities of amphiphilic cationic polymers and their efficacy of combination with novobiocin 査読あり 国際誌
Miyagawa, A., Ohno, S., Hattori, T., Yamamura, H
Journal of Biomaterials Science, Polymer Edition 2021年10月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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N, N-Bis (hexyl α-d-acetylmannosyl) Acrylamide 査読あり 国際誌
Atsushi Miyagawa, Shinya Ohno, Hatsuo Yamamura
Molbank 2021 ( 3 ) M1255 2021年07月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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One-Step Synthesis of Sugar Nucleotides 査読あり 国際誌
Atsushi Miyagawa, Sanami Toyama, Ippei Ohmura, Shun Miyazaki, Takeru Kamiya, Hatsuo Yamamura
J. Org. Chem. 85 15645 - 15651 2020年11月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Synthesis of β-1,3-glucan mimics by β-1,3-glucan trisaccharyl monomer polymerization 査読あり 国際誌
Atsushi Miyagawa, Hatsuo Yamamura
Carbohydrate Polymers 227 115105 2020年01月
記述言語：英語 掲載種別：研究論文（学術雑誌）
β-1,3-Glucans are important as immunostimulating agents in living organisms. The multivalent binding ofβ-1,3glucans to dectin-1, a cell surface receptor, activates immunological defenses. To study artificial immunostimulating agents, glycopolymers carrying β-1,3-glucan trisaccharides as artificial ligands were synthesized. The β-1,3-glucan trisaccharide, defined as an active unit of β-1,3-glucan, was constructed from D-glucose by glycosylation. A norbornene group was introduced as a polymerizable group into the trisaccharide derivative at the aglycone. The prepared endo/exo norbornene stereoisomers of the monomers were separated by silica gel chromatography and identified by NMR spectroscopy and mass spectrometry. The synthesized glycosyl monomers were polymerized and copolymerized with norbornene using 2nd generation Hoveyda-Grubbs catalyst, deprotected, and purified by gel filtration to prepare water-soluble glycopolymers of varied compositions and high molecular weights. These polymers will have the potential for multivalent binding to dectin-1 to activate immune response and facilitate studies to understand the binding mechanisms of β-1,3-glucans with dectin-1.
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Gramicidin S-inspired Antimicrobial Cyclodextrin to Disrupt Gram-negative and Gram-positive Bacterial Membranes 査読あり 国際誌
Hatsuo Yamamura, Kana Isshiki, Yusuke Fujita, Hisato Kato, Takashi Katsu, Kazufumi Masuda, Kayo Osawa, Atsushi Miyagawa
MedChemComm 10 ( 10 ) 1432 - 1437 2019年08月
担当区分：筆頭著者 記述言語：英語 掲載種別：研究論文（学術雑誌）
A membrane-active antimicrobial peptide gramicidin S-like amphiphilic structure was prepared from cyclodextrin. The mimic was a cyclic oligomer composed of 6-amino-modified glucose 2,3-di-O-propanoates and it exhibited antimicrobial activity against Gram-positive and Gram-negative bacteria, together with no resistance development and low haemolytic activity against red blood cells.
DOI： 10.1039/C9MD00229D
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Development of New Antimicrobial Agents from Cationic PG-surfactants containing oligo-Lys peptides 査読あり
Kimura Ryosuke, Shibata Masahide, Koeda Shuhei, Miyagawa Atsushi, Yamamura Hatsuo Mizuno Toshihisa
Bioconjugate Chemistry 2018年12月
記述言語：英語 掲載種別：研究論文（学術雑誌）
Peptide gemini-surfactant (PG-surfactant), a kind of lipopeptide, is composed of a short linker peptide (X) between two alkyl-chain-modified Cys residues, and peripheral peptides at the N-terminal (Y) and the C-terminal (Z) sides, respectively, of the alkylated
Cys residues. In this study, we developed and examined a series of PG-surfactants containing two C12 saturated alkanes and oligo-Lys, arranged at the X-, Y-, or Z-positions. To arrange oligo-Lys at the Y- or Z-positions, a repeat sequence of -Asp-Lys-Asp-Lys-
was used at the X-position. All of the PG-surfactants exhibited high antimicrobial activity against both gram-positive and negative bacteria. In addition to high antimicrobial activity, a low hemolysis activity is prerequisite for efficient intravenous administration.
Among the synthesized PG-surfactants, those having -(Lys)3- at the Y- or Z-positions, i.e. K3-DKDKC12 and DKDKC12-K3, showed reasonably low hemolytic activities. This combination of high antimicrobial activity along with low hemolytic activity is an
essential and unique property, and has not been previously reported for the synthesized lipopeptides. Further, using scanning electron microscope (SEM) and N-phenyl-1-naphthylamine (NPN) uptake assay we showed that the antimicrobial activity of these PG-surfactants may be attributed to membrane disruptive mechanisms. Although the PG-surfactants with low hemolytic activity could interact and localize onto red blood cell surfaces, and cause slight expansion of cell morphologies, no subsequent penetration occurred. In summary, we describe here the successful development of PG-surfactants having high antibacterial and low hemolytic activity, thus providing a significant molecular platform to develop novel antimicrobial agents. -
Transglycosylation Activity of Catalytic Domain Mutant of Endo-1,3-β-glucanase from Cellulosimicrobium Cellulans 査読あり 国際誌
Y. Hantani, S. Motoki, A. Miyagawa, H. Yamamura, M.Oda
Protein & Peptide Letters 25 1 - 5 2018年07月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Membrane-Active Antimicrobial Poly(Amino-Modified Alkyl) beta-Cyclodextrins Synthesized via Click Reactions 査読あり 国際誌
Hatsuo Yamamura, Miho Nonaka, Shingo Okuno, Ryogo Mitsuhashi, Hisato Kato, Takashi Katsu, Kazufumi Masuda, Koichi Tanimoto,Haruyoshi Tomita, Atsushi Miyagawa
MedChemComm 9 509 - 518 2018年03月
担当区分：筆頭著者 記述言語：英語 掲載種別：研究論文（学術雑誌）
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Membrane-active antimicrobial poly(amino-modified alkyl) β-cyclodextrins synthesized: Via click reactions 査読あり
Hatsuo Yamamura, Miho Nonaka, Shingo Okuno, Ryogo Mitsuhashi, Hisato Kato, Takashi Katsu, Kazufumi Masuda, Koichi Tanimoto, Haruyoshi Tomita, Atsushi Miyagawa
MedChemComm 9 ( 3 ) 509 - 518 2018年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Royal Society of Chemistry
The emergence of drug-resistant bacteria has led to the high demand for new antibiotics. In this report, we investigated membrane-active antimicrobial β-cyclodextrins. These contain seven amino-modified alkyl groups on a molecule, which act as functional moieties to permeabilize bacterial cell membranes. The polyfunctionalization of cyclodextrins was achieved through a click reaction assisted by microwave irradiation. A survey using derivatives with systematically varied functionalities clarified the unique correlation of the antimicrobial activity of these compounds with their molecular structure and hydrophobicity/hydrophilicity balances. The optimum hydrophobicity for the compounds being membrane-active was specific to bacterial strains and animal cells
this led to specific compounds having selective toxicity against bacteria including multidrug-resistant pathogens. The results demonstrate that cyclodextrin is a versatile molecular scaffold for rationally designed structures and can be used for the development of new antibiotics.DOI： 10.1039/c7md00592j
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Hatsuo Yamamura, Takahiro Mabuchi, Tomoki Ishida, Atsushi Miyagawa
Chemical Biology & Drug Design 90 ( 5 ) 1012 - 1018 2017年11月
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Chemical Synthesis and Isolation of UDP-2-Deoxy Glucose and Galactose 査読あり 国際誌
Atsushi Miyagawa, Shunya Takeuchi, Shinji Itoda, Sanami Toyama, Kenta Kurimoto, Hatsuo Yamamura,Yukishige Ito
Synthetic Communication 46 1790 - 1795 2016年08月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Aglycone Specificity of Endo-ß- 1,3-Glucanase 査読あり 国際誌
Atsushi Miyagawa, Takahiro Yamaguchi, Yoichi Tanabe, Masayuki Oda, Hatsuo Yamamura
JSM Chem 4 ( 2 ) 1026 2016年06月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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2II-VII, 3I-VII, 6I-VII-Icosa-O-acetyl-2I-deoxy-cyclomaltoheptaose 査読あり 国際誌
Atsushi Miyagawa, Kazuki Kano, Aya Yoshida, Hatsuo Yamamura
Molbank ( 2 ) M900 2016年03月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Sialylation with systematically protected allyl galactoside acceptors using sialyl phosphate donors 査読あり 国際誌
Kenta Kurimoto, Hatsuo Yamamura, Atsushi Miyagawa
Tetrahedron Letters 57 1442 - 1445 2016年03月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Rule of Hydrophobicity/Hydrophilicity Balance in Membrane-Disrupting Antimicrobial Activity of Polyalkylamino Cyclodextrins Synthesized via Click Chemistry 査読あり 国際誌
Hatsuo Yamamura, Atsushi Miyagawa, Hiroki Sugiyama, Kensuke Murata,Takahiro Mabuti, Ryogo Mitsuhashi, Tatsuya Hagiwara, Miho Nonaka,Koichi Tanimoto, Haruyoshi Tomita
Chemistry Select 1 ( 3 ) 469 - 472 2016年03月
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Sialylation with systematically protected allyl galactoside acceptors using sialyl phosphate donors 査読あり
Kenta Kurimoto, Hatsuo Yamamura, Atsushi Miyagawa
TETRAHEDRON LETTERS 57 ( 13 ) 1442 - 1445 2016年03月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD
Various N-protected sialyl donors were synthesized and utilized in sialylation to investigate the reactivity and stereoselectivity of sialyl phosphate donors. Furthermore, in order to understand the effects of protecting groups and hydroxyl group positions on galactosyl acceptors, the sialylation efficiencies of all of the hydroxy groups on galactoses, which were protected with benzyl or benzoyl groups, were investigated. Consequently, the sialylation of N-acetyl-5-N,4-O-oxazolidinone-protected sialyl phosphate donors with allyl galactosides was accomplished and gave the GM4 regioisomers. (C) 2016 Elsevier Ltd. All rights reserved.
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Selective Deprotection of Trityl Group on Carbohydrate by Microflow Reaction Inhibiting Migration of Acetyl Group 査読あり 国際誌
Atsushi Miyagawa, Ryusuke Tomita, Kenta Kurimoto, Hatsuo Yamamura
Synthetic Communication 46 556 - 562 2016年02月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Functionalization of Aglycones on Sialoside Derivatives to Generate Precursors for Biological Applications 査読あり 国際誌
Kenta Kurimoto, Hatsuo Yamamura, Atsushi Miyagawa
Chemistry Letters 45 ( 2 ) 128 - 130 2016年02月
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Selective deprotection of trityl group on carbohydrate by microflow reaction inhibiting migration of acetyl group 査読あり
Atsushi Miyagawa, Ryusuke Tomita, Kenta Kurimoto, Hatsuo Yamamura
SYNTHETIC COMMUNICATIONS 46 ( 6 ) 556 - 562 2016年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：TAYLOR & FRANCIS INC
The trityl group is an important and useful protecting group for primary hydroxy groups on carbohydrates. However, during deprotection, neighboring acetyl groups can easily migrate to the deprotected hydroxy groups. Hence, deprotection of trityl groups was optimized using a microreactor with regard to flow rate, reagent concentration, reaction time, and substrate concentration. The optimized microflow reaction conditions inhibited migration and could be applied to large-scale reactions and other substrates.
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Chemical synthesis and isolation of UDP-2-deoxy glucose and galactose 査読あり
Atsushi Miyagawa, Shunya Takeuchi, Shinji Itoda, Sanami Toyama, Kenta Kurimoto, Hatsuo Yamamura, Yukishige Ito
SYNTHETIC COMMUNICATIONS 46 ( 22 ) 1790 - 1795 2016年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：TAYLOR & FRANCIS INC
2-Deoxy sugars are attractive compounds in synthetic chemistry with regard to reactivity and stereoselectivity. Moreover, their ability to inhibit enzymes and metabolism is significant in biology. In this study, uridine-5-diphosphate (UDP)-2-deoxy glucose (11) and galactose (12) were synthesized chemically. These sugar donors for glycosyltransferases were obtained -selectively via phosphorylation using thioglycosides, coupling reaction with uridine-5-monophosphate (UMP)-morpholidate, and moderate deacetylation. Isolation was carried out by sequential silica-gel chromatography using two kinds of developing solvents in a refrigerator. The structures were elucidated from the NMR results. Investigation of stability showed that the synthesized UDP-2-deoxy sugars were hydrolyzed much faster in buffer (pH 4) than the natural UDP sugars.
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Synthesis of Branched Tetrasaccharide Derivatives of Schizophyllan-like β-Glucan 査読あり 国際誌
Atsushi Miyagawa, Tomoka Matsuda, Hatsuo Yamamura
Journal of Carbohydrate Chemistry 34 ( 5 ) 215 - 246 2015年07月
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Polysulfonylated cyclodextrins. Part 14. Structural validation of tris- and pentakis(6-O-mesitylsulfony)cyclomaltooctaose isomers by 1H-NMR spectrometry 査読あり 国際誌
Hatsuo Yamamura, Mutsumi Watanabe, Sho Kawahara, Atsushi Miyagawa, and Masao Kawai
Magnetic Resonance in Chemistry 53 237 - 243 2015年03月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Polysulfonylated cyclodextrins. Part 14. Structural validation of tris-and pentakis(6-O-mesitylsulfony)cyclomaltooctaose isomers by H-1-NMR spectrometry 査読あり
Hatsuo Yamamura, Mutsumi Watanabe, Sho Kawahara, Atsushi Miyagawa, Masao Kawai
MAGNETIC RESONANCE IN CHEMISTRY 53 ( 3 ) 237 - 243 2015年03月
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Chemical approach for the syntheses of GM4 isomers with sialic acid to non-natural linkage positions on galactose 査読あり 国際誌
Kenta Kurimoto, Hatsuo Yamamura, Atsushi Miyagawa
Carbohydrate Research 401 39 - 50 2015年01月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Chemical approach for the syntheses of GM4 isomers with sialic acid to non-natural linkage positions on galactose 査読あり
Kenta Kurimoto, Hatsuo Yamamura, Atsushi Miyagawa
CARBOHYDRATE RESEARCH 401 39 - 50 2015年01月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：ELSEVIER SCI LTD
Cell-surface glycans containing sialic acid are involved in various biological phenomena. However, the syntheses of GM4 derivatives with (2 >2) and (2 >4) linkages have not been investigated to date. In this study, sialylation of all of the hydroxyl groups on galactose were investigated for the syntheses of GM4 isomers. Regioselective sialylation was achieved via protection of galactosyl acceptors using electron-rich benzyl groups. These synthetic sialylated glycans will prove to be useful tools for studying unidentified carbohydrate-mediated biological roles. (C) 2014 Elsevier Ltd. All rights reserved.
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Synthesis of Antimicrobial Cyclodextrins Bearing Polyarylamino and Polyalkylamino Groups via Click Chemistry for Bacterial Membrane Disruption 査読あり
Hatsuo Yamamura他
Chem. Commun. 50 ( 41 ) 5444 - 5446 2014年05月
担当区分：筆頭著者 記述言語：英語 掲載種別：研究論文（学術雑誌）
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Synthesis of antimicrobial cyclodextrins bearing polyarylamino and polyalkylamino groups via click chemistry for bacterial membrane disruption 査読あり
Hatsuo Yamamura, Yuuki Sugiyama, Kensuke Murata, Takanori Yokoi, Ryuji Kurata, Atsushi Miyagawa, Kenji Sakamoto, Keiko Komagoe, Tsuyoshi Inoue, Takashi Katsu
CHEMICAL COMMUNICATIONS 50 ( 41 ) 5444 - 5446 2014年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：ROYAL SOC CHEMISTRY
Cyclodextrin derivatives are synthesized as membrane-disrupting agents via a microwave-assisted Huisgen reaction. Their ability to permeabilize bacterial membranes depends on the amino substituents and an appropriate balance of hydrophobicity and hydrophilicity, thus enabling the preparation of derivatives with selective toxicity against bacteria.
DOI： 10.1039/c3cc49543d
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Unique, Fast, and All-or-none Click Reaction on Cyclodextrin and Amylose 査読あり
Yamamura Hatsuo, Miyagawa Atsushi
Chemistry Letters ( 6 ) 643 - 645 2013年06月
担当区分：筆頭著者 記述言語：英語 掲載種別：研究論文（学術雑誌）
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Unique, Fast, and All-or-none Click Reaction on Cyclodextrin and Amylose 査読あり
Hatsuo Yamamura, Kyohei Shimohara, Ryuji Kurata, Yusuke Fujita, Kensuke Murata, Takaaki Hayashi, Atsushi Miyagawa
CHEMISTRY LETTERS 42 ( 6 ) 643 - 645 2013年06月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：CHEMICAL SOC JAPAN
The chemical polymodification of cyclodextrins and amyloses proceeded quickly with use of the microwave-assisted Huisgen reaction in an all-or-none fashion without the formation of less-modified by-products.
DOI： 10.1246/cl.130095
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Mimicking an antimicrobial peptide polymyxin B by use of cyclodextrin 査読あり
Hatsuo Yamamura, Ken Suzuki, Kazuma Uchibori, Atsushi Miyagawa, Masao Kawai, Chie Ohmizo, Takashi Katsu
CHEMICAL COMMUNICATIONS 48 ( 6 ) 892 - 894 2012年01月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：ROYAL SOC CHEMISTRY
Cyclodextrin derivatives prepared to mimic a membrane active antibacterial peptide polymyxin B strongly permeabilized bacterial membrane and inhibited bacterial proliferation.
DOI： 10.1039/c1cc16369h
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Mimicking an Antimicrobial Peptide Polymyxin B by Use of Cyclodextrin 査読あり
Hatsuo Yamamura, Atsushi Miyagawa,他
Chem. Commun. 48 ( 6 ) 892 - 894 2012年
担当区分：筆頭著者 記述言語：英語 掲載種別：研究論文（学術雑誌）
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gamma-Cyclodextrins possessing an azido group and a triisopropylbenzenesulfonyl group as useful synthetic and authentic intermediates for unsymmetrically functionalized derivatives 査読あり
Yoshihide Himeno, Atsushi Miyagawa, Masao Kawai, Hatsuo Yamamura
TETRAHEDRON 65 ( 45 ) 9474 - 9480 2009年11月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD
Seven isomers of cyclomaltooctaose (gamma-cyclodextrin) whose C6s were unsymmetrically disubstituted with both an azido group and an arenesulfonyloxy group were prepared and each of them was isolated by reversed phase chromatography. The assignment of the modified positions in each regioisomers was unambiguously performed by chemical correlation with the authentic compounds and chemical conversion to the 3,6-anhydro derivatives followed by high-resolution 2D-(1)H NMR (COSY, TOCSY, and HO-HAHA) analyses. The compounds are versatile synthetic and authentic intermediates to prepare sophisticated derivatives with two different functionalities at desired positions on the molecule for supramolecular chemistry. (C) 2009 Elsevier Ltd. All rights reserved.
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Preparation of a cyclodextrin dimer linked with a bis(picolinyl)cystine moiety and its intra- and intermolecular inclusion behavior 査読あり
Hatsuo Yamamura, Kousuke Satake, Rieko Hirasawa, Shinichi Yamada, Masao Kawai
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY 57 ( 1-4 ) 261 - 264 2007年04月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：SPRINGER
A novel cyclodextrin (CD) dimer linked with a bis(picolinyl)cystine (Cys) moiety was prepared by the coupling of Boc-protected Cys with amino-modified CDs, followed by deprotection of the Boc groups and bispicolinylation. The dimer showed less affinity to an organic guest molecule compared to that of a native CD monomer. It was attributed to an intramolecular inclusion of the pyridine moiety into CD cavity. The dimer caused significant increase of its organic guest affinity by an addition of a copper ion. The included pyridine group may come out of a CD cavity to bind the copper ion and the two CDs included cooperatively and intermolecularly a guest molecule with high affinity.
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Complexation and Chiral recognition Thermodynamics of g-Cyclodextrin with N-Acetyl- and N-Carbobenzyloxy-depetides Possessing Two Aromatic Rings 査読あり
Rekharsky, M. V.; Yamamura, H.; Kawai, M.; Inoue, Y.
J. Org. Chem 13 5228 - 5235 2003年04月
掲載種別：研究論文（学術雑誌）
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Preparation of Hexakis(6-O-mesitylsulfonyl)cyclomaltooctaoses and Structural Validation of the Four Isomers Using Heteronuclear Multiple Bond Correlation Spectroscopy 査読あり
Yamamura, H.; Miyachi, S.; Kano, K.; Araki, S.; Lee, K.; Kawai, M.; Ueyama, N.
Bull. Chem. Soc. Jpn 76 171 - 175 2003年04月
掲載種別：研究論文（学術雑誌）
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Preparation of b-Cyclodextrin Derivatives Possessing two Trimethylammonio Groups on Their Primary Hydroxy Sides as Chiral Selectors 査読あり
Yamamura , H.; Yamada, Y.; Mitagi, R.; Kano, K.; Araki, S.; Kawai, M.
J. Inclusion Phenom. Macrocyclic Chem 45 211 - 216 2003年04月
掲載種別：研究論文（学術雑誌）
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Extra Amino Group-containing Gramicidin S analogs PossessingOuter Membrane-permeabilizing Activ 査読あり
Kawai, M.; Tanaka, R.; Yamamura, H.; Yasuda, K.; Narita, S.; Umemoto, H.; Ando, S.; Katsu, T.
Chem. Commun 1264 - 1265 2003年04月
掲載種別：研究論文（学術雑誌）
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Cytotoxic Activity of Physalins Possessing modified Skeletal Structures against HeLa Cells 査読あり
Makino, B.; Ohya, J.; Yamamura, H.; Araki, S.; Butsugan, Y; Kawai, M.
Pharmazie 58 70 - 71 2003年04月
掲載種別：研究論文（学術雑誌）
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Preparation of beta-cyclodextrin derivatives possessing two trimethylammonio groups on their primary hydroxy sides as chiral guest selectors 査読あり
H Yamamura, Y Yamada, R Miyagi, K Kano, S Araki, M Kawai
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY 45 ( 3-4 ) 211 - 216 2003年04月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：SPRINGER
Three isomers of beta-cyclodextrin derivatives 2a-c possessing two trimethylammonio groups on their C(6) atoms were prepared by reaction of the corresponding regioisomers of diamino compounds with methyl iodide. These derivatives recognize chiral guests through three-point interactions composed of both Coulomb interactions by the two cationic moieties and hydrophobic interaction by the molecular cavity.
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Preparation of β-Cyclodextrin Derivatives Possessing Two Trimethylammonio Groups on Their Primary Hydroxy Sides as Chiral Guest Selectors 査読あり
Hatsuo Yamamura, Yuichi Yamada, Rie Miyagi, Kazuaki Kano, Shuki Araki, Masao Kawai
Journal of Inclusion Phenomena 45 ( 3-4 ) 211 - 216 2003年04月
記述言語：英語 掲載種別：研究論文（学術雑誌）
Three isomers of β-cyclodextrin derivatives 2a-c possessing two trimethylammonio groups on their C(6) atoms were prepared by reaction of the corresponding regioisomers of diamino compounds with methyl iodide. These derivatives recognize chiral guests through three-point interactions composed of both Coulomb interactions by the two cationic moieties and hydrophobic interaction by the molecular cavity.
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Extra amino group-containing gramicidin S analogs possessing outer membrane-permeabilizing activity 査読あり
M Kawai, R Tanaka, H Yamamura, K Yasuda, S Narita, H Umemoto, S Ando, T Katsu
CHEMICAL COMMUNICATIONS ( 11 ) 1264 - 1265 2003年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：ROYAL SOC CHEMISTRY
Novel (2S,4R)- and (2S,4S)-4-aminoproline residue-containing analogs of the cyclic decapeptide antibiotic gramicidin S were synthesized, which exhibited marked permeabilizing activity on the outer membrane of gram-negative bacteria.
DOI： 10.1039/b302351f
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Preparation of hexakis(6-O-mesitylsulfonyl)cyclomaltooctaoses and structural validation of the four isomers using heteronuclear multiple bond correlation spectroscopy 査読あり
Hatsuo Yamamura, Sadaichi Miyachi, Kazuaki Kano, Shuki Araki, Kenichi Lee, Masao Kawai, Norikazu Ueyama
Bulletin of the Chemical Society of Japan 76 ( 1 ) 171 - 175 2003年
記述言語：英語 掲載種別：研究論文（学術雑誌）
Four cyclomaltooctaose derivatives 1a-d, which possess six mesitylsulfonyloxy groups on their C(6) atoms, were prepared. The assignment of the regiosiomers was performed by observing the long-range coupling through a glycoside linkage between H(1′)-C(4) and C(1′)-H(4) using a heteronuclear multiple-bond correlation (HMBC) method.
DOI： 10.1246/bcsj.76.171
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Stereochemistry of Protected Ornithine Side Chains of Gramicidin S Derivatives: X-ray Crystal Structure of the Bis-Boc-tetra-N-methyl Derivative of Gramicidin S 査読あり
Yamada, K.; Unno, M.; Kobayashi, K.; Oku, H.; Yamamura, H.; Araki, S.; Matsumoto, H.; Katakai, R.; Kawai M.
J. Am. Chem. Soc 124 12684 - 12686 2002年04月
掲載種別：研究論文（学術雑誌）
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Cytotoxic Activity of Physalins and Related Compounds against HeLa Cells 査読あり
Kawai, M.; Makino, B.; Yamamura, H.; Araki, S.; Butsugan, Y.; Ohya, J.
Pharmazie 57 348 - 350 2002年04月
掲載種別：研究論文（学術雑誌）
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Tautomerism between Exomethylene Type Physalins and Oxymethylene-bridged Physalins 査読あり
Makino, B.; Kawai, M.; Yamamura, H.; Araki, B.; Butsugan, Y.
Pharmazie 57 215 - 216 2002年04月
掲載種別：研究論文（学術雑誌）
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Cytotoxic activity of physalins and related compounds against HeLa cells 査読あり
M. Kawali, B. Makino, H. Yamamura, S. Araki, Y. Butsugan, J. Ohya
Pharmazie 57 ( 5 ) 348 - 350 2002年
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Tautomerism between exomethylene type physalins and oxymethylene-bridged physalins 査読あり
B. Makino, Masao Kawai, H. Yamamura, S. Araki, Y. Butsugan
Pharmazie 57 ( 3 ) 215 - 216 2002年
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Shuki ARAKI, Hiromi HATTORI, Koji OGAWA, Masashi KUZUYA, Tomoko INOUE, Hatsuo YAMAMURA, Masao KAWAI
J. Chem. Soc., Perkin Trans.1 2476 - 2482 2001年04月
掲載種別：研究論文（学術雑誌）
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Critical Difference in Chiral Recognition of N-Cbz-D/L-aspartic and -glutamic Acids by Mono- and Bis(trimethylammonio)-beta-cyclodextrins. 査読あり
Mikhail REKHARSKY, Hatsuo YAMAMURA, Masao KAWAI, Yoshihisa INOUE
J. Am. Chem. Soc. 123 5360 - 5361 2001年04月
掲載種別：研究論文（学術雑誌）
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Capillary Zone Eelectrophoretic Chiral Discrimination Using Cationic Cyclodextrin Dderivative. Determination of Velocity andAssociation Constants of Each Enantiomer of Amino Acid Derivative with 6-Trimethylammonio-deoxy-beta-cyclodextrin 査読あり
Hatsuo YAMAMURA, Asako AKASAKI, Yuichi YAMADA, Kazuaki KANO, Takao Katsuhara, Shuki ARAKI, Masao KAWAI, Takao TSUDA
Electrophoresis 22 478 - 483 2001年04月
掲載種別：研究論文（学術雑誌）
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Calorimetric and NMR Studies on the Direct Correlation between Supramolecular Complex Structure and the Thermodynamics ofN-Benzyloxycarbonyl-L-aspartic and -glutamic Acids Inclusion with Mono- and Bis(trimethylammonio)-beta-cyclodextrins 査読あり
Hatsuo YAMAMURA, Mikhail REKHARSKY, Asako AKASAKI, Shuki ARAKI, Masao KAWAI, Yoshihisa INOUE
J. Phys. Org. Chem. 14 416 - 424 2001年04月
掲載種別：研究論文（学術雑誌）
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Allylindation of Cyclopropenes in Organic and Aqueous Media:Switching the Regio- and Stereoselectivity Based on the Chelation with aHydroxy Group and the Crystal Structure of the Cyclopropylindium Product 査読あり
Shuki ARAKI, Fumio SHIRAKI, Takashi TANAKA, Hiroyuki NAKANO, Kandasamy Subburaj, Tsunehisa HIRASHITA, Hatsuo YAMAMURA, MasaoKAWAI
Chem. Eur. J. 7 ( 13 ) 2784 - 2790 2001年04月
掲載種別：研究論文（学術雑誌）
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Tsunehisa HIRASHITA, Hatsuo YAMAMURA, Masao KAWAI, Shuki ARAKI
Chem. Commun. 387 - 388 2001年04月
掲載種別：研究論文（学術雑誌）
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Zinc Bromide-Promoted Tosylation of Alcohols Allows Efficient Temperature-Controlled Primary Hydroxy Sulfonylation 査読あり
Hatsuo YAMAMURA, Jyumpei KAWASAKI, Hirokazu SAITO, Shuki ARAKI, Masao KAWAI
Chem. Lett 706 - 708 2001年04月
掲載種別：研究論文（学術雑誌）
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The Structure of Physalin T from Physalis Alkekengi var. Francheti. 査読あり
Masao KAWAI, Tatsuo YAMAMMOTO, Bunsho MAKINO, Hatsuo YAMAMURA, Shuki ARAKI, Yasuo BUTSUGAN, Kazuki SAITO
J. Asian Natural Products Research 3 199 - 205 2001年04月
掲載種別：研究論文（学術雑誌）
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A new cascade for the one-pot synthesis of linear homoallylic alcohols with an allylic diindium reagent 査読あり
T Hirashita, H Yamamura, M Kawai, S Araki
CHEMICAL COMMUNICATIONS ( 4 ) 387 - 388 2001年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：ROYAL SOC CHEMISTRY
A new cascade based on a novel allylic diindium reagent has been developed; the indium reagent prepared from 3-bromo-1-iodopropene successively coupled with carbonyl compounds and then with aryl, alkenyl or allyl halides in the presence of a Pd(0) catalyst to afford a convenient one-pot synthesis of linear homoallylic alcohols.
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Zinc bromide-promoted tosylation of alcohols allows efficient temperature-controlled primary hydroxy sulfonylation 査読あり
Hatsuo Yamamura, Jyumpei Kawasaki, Hirokazu Saito, Shuki Araki, Masao Kawai
Chemistry Letters ( 7 ) 706 - 707 2001年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Chemical Society of Japan
The combination of zinc bromide with tosyl chloride promoted sulfonylation, allowing temperature-controlled regioselective sulfonylation of carbohydrates which possess both primary and secondary hydroxy groups.
DOI： 10.1246/cl.2001.706
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The structure of physalin T from Physalis alkekengi var. francheti 査読あり
M Kawai, T Yamamoto, B Makino, H Yamamura, S Araki, Y Butsugan, K Saito
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH 3 ( 3 ) 199 - 205 2001年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：HARWOOD ACAD PUBL GMBH
A new steroidal constituent named physalin T (3) was isolated from the aqueous extract of Physalis alkekengi var. francheti. Based on H-1 and C-13 NMR spectral studies the structure was assigned as 2,3-dihydrophysalin D, i.e., 5 alpha ,6 beta -dihydroxy-2,3,5,6-tetrahydrophysa B, which is the first example of a natural physalin possessing a saturated ring A moiety. The structure was confirmed by the chemical transformation from the known physalin D (2) to physalin T.
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The photochemical reactions of nitrogen-rich mesoionic 1,3-diphenyltetrazolium heterocycles and related compounds 査読あり
Shuki Araki, Hiromi Hattori, Koji Ogawa, Masashi Kuzuya, Tomoko Inoue, Hatsuo Yamamura, Masao Kawai
Journal of the Chemical Society. Perkin Transactions 1 1 ( 19 ) 2476 - 2482 2001年
記述言語：英語 掲載種別：研究論文（学術雑誌）
Photochemical reactions of azo and triazo derivatives of mesoionic 1,3-diphenyltetrazolium heterocycles and related compounds were studied. The reaction paths were found to depend markedly on the types of substrate, substituent and reaction solvent giving diverse products. Upon irradiation of the 1,1′3,3′-tetraphenylazoditetrazolium salt 1, the addition of hydrogen and acetone to the N-N bond was observed in methanol and acetone, respectively, whereas the bond was cleaved in diethyl ketone to give the 5-aminotetrazolium salt 10. The corresponding radical cation 11 also gave the reduction product in methanol. On the other hand, the 1,3-diphenyl-5-(phenylazo)tetrazolium salt 12 underwent nitrogen evolution giving the 1,3-diphenyltetrazolium salt 13 via the corresponding tetrazolium radical. Triazene derivatives 14 and 17 underwent an N–N bond cleavage to give tetrazolio-5-amide 4. The mesoionic triazene compounds bearing a tosyl 18 or cyano group 19 gave products 20 and 23. Triphenylphosphinotriazene 24 liberated nitrogen to give phosphinoimide 25 and its hydrolysis product 10. Tetrazolylamide 26 lost a phenyldiazonium group from the 1,3-diphenyltetrazolium ring to give the guanidine derivative 27. © 2001 The Royal Society of Chemistry.
DOI： 10.1039/b009526p
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Capillary zone electrophoretic chiral discrimination using a cationic cyclodextrin derivative: Determination of velocity and association constants of each enantiomer of the amino acid derivative with 6-trimethylammonio-deoxy-β-cyclodextrin 査読あり
Hatsuo Yamamura, Asako Akasaki, Yuichi Yamada, Kazuaki Kano, Takao Katsuhara, Shuki Araki, Masao Kawai, Takao Tsuda
Electrophoresis 22 ( 3 ) 478 - 483 2001年
記述言語：英語 掲載種別：研究論文（学術雑誌）
A positively charged β-cyclodextrin possessing a trimethylammonio group, 6-trimethylammonio-6-deoxy-β-cyclodextrin chloride 1 was prepared by the reaction of an amino derivative 3 with methyl iodide under very mild conditions. The cyclodextrin derivative discriminated between enantiomers of acetylphenylalanine 2 on capillary zone electrophoresis (CZE) analysis, which was possibly due to an electrostatic interaction between the trimethylammonio group of 1 and the carboxylate group of 2, and also due to the inclusion of 2 in a hydrophobic molecular cavity of 1. Double data normalization based on relative electrophoretic velocity of peaks due to indirect response of 1 and also water in an injected sample may be effective for elimination of variation and fluctuation of physical parameters of medium, such as viscosity and ionic strength, in order to determine intrinsic association constants and velocity of the complexes.
DOI： 10.1002/1522-2683(200102)22:3<478::AID-ELPS478>3.0.CO;2-L
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Calorimetric and NMR studies on the direct correlation between supramolecular complex structure and the thermodynamics of N-benzyloxycarbonyl-L-aspartic and -glutamic acid inclusion complexes with mono- and bis(trimethylammonio)-β-cyclodextrins 査読あり
Hatsuo Yamamura, Mikhail Rekharsky, Asako Akasaki, Schuki Araki, Masao Kawai, Yoshihisa Inoue
Journal of Physical Organic Chemistry 14 ( 7 ) 416 - 424 2001年
記述言語：英語 掲載種別：研究論文（学術雑誌）
The stability constants and standard Gibbs energy, enthalpy and entropy changes for the 1:1 inclusion complexation of N-benzyloxycarbonyl-L-aspartic and -glutamic acids with native β-cyclodextrin (β-CD), mono(6-amino-6-deoxy)-β-CD, mono(6-trimethylammonio-6-deoxy)-β-CD and A,B-, A,C- and A,D-bis(6-trimethylammonio-6-deoxy)-β-CDs were determined in aqueous phosphate buffer (pH 6.9) at 298.15 K by titration microcalorimetry. The supramolecular complex structures were elucidated from 1D and 2D NMR spectra, including ROESY, COSY and HOHAHA techniques. Combining the results obtained from the microcalorimetric and NMR studies, we elucidated not only the detailed complex structures and the thermodynamic consequences, but also the mutual dependence between the complex structure and the overall complexation thermodynamics. Copyright © 2001 John Wiley &
Sons, Ltd.DOI： 10.1002/poc.381
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Synthesis of New Tricyclic Mesoionic Amides via Photochemical Conversion of a 5-Azido-1-mesityl-3-phenyltetrazolium Salt 査読あり
Shuki ARAKI, Hiromi HATTORI, Hatsuo YAMAMURA, Masao KAWAI
J. Heterocyclic Chem. 37 1129 - 1134 2000年04月
掲載種別：研究論文（学術雑誌）
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Keiichi YAMADA, Yu-ichi TAKAHASHI, Hatsuo YAMAMURA, Shuki ARAKI, Masao KAWAI
J. Chem. Soc., Chem. Commun 1315 - 1316 2000年04月
掲載種別：研究論文（学術雑誌）
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A New Preparative Method for Allylic Indium (III) Reagents by Reductive Transmetalation of p-Allylpalladium (II) with Indium (I) Salts 査読あり
Shuki ARAKI, Toshiya KAMEI, Tsunehisa HIRASHITA, Hatsuo YAMAMURA, Masao KAWAI
Organic Lett 2 847 - 849 2000年04月
掲載種別：研究論文（学術雑誌）
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A Facile Preparation of Indium Enolates and Their Reformatsky-and Darzens-type Reactions 査読あり
Tsunehisa HIRASHITA, Kenji KINOSHITA, Hatsuo YAMAMURA, Masao KAWAI, Shuki ARAKI
J. Chem. Soc., Perkin Trans 1 825 - 828 2000年04月
掲載種別：研究論文（学術雑誌）
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A facile preparation of indium enolates and their Reformatsky- and Darzens-type reactions 査読あり
T Hirashita, K Kinoshita, H Yamamura, M Kawai, S Araki
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 ( 5 ) 825 - 828 2000年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：ROYAL SOC CHEMISTRY
Indium enolates were readily prepared by transmetalation of lithium enolates with indium trichloride, and were subsequently reacted with aldehydes to give beta-hydroxy esters in high yields. Indium alpha-bromo enolates were also prepared and reacted with carbonyl compounds to give Darzens-type alpha,beta-epoxy carbonyl products.
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Phosphodiester bond cleavage mediated by a cyclic beta-sheet peptide-based dinuclear zinc(II) complex 査読あり
K Yamada, Y Takahashi, H Yamamura, S Araki, K Saito, M Kawai
CHEMICAL COMMUNICATIONS ( 14 ) 1315 - 1316 2000年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：ROYAL SOC CHEMISTRY
A dinuclear Zn(II) complex of N-2 delta,N-2 delta,N-2'delta,N-2'delta-tetrakis(2-pyridylmethyl) derivative of cyclic peptide gramicidin S markedly accelerated the cleavage of the phosphodiester linkage of the RNA model substrate 2-hydroxypropyl p-nitrophenyl phosphate.
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A facile preparation of indium enolates and their Reformatsky-and Darzens-type reactions 査読あり
Tsunehisa Hirashita, Kenji Kinoshita, Hatsuo Yamamura, Masao Kawai, Shuki Araki
Journal of the Chemical Society, Perkin Transactions 1 ( 5 ) 825 - 828 2000年
記述言語：英語 掲載種別：研究論文（学術雑誌）
Indium enolates were readily prepared by transmetalation of lithium enolates with indium trichloride, and were subsequently reacted with aldehydes to give β-hydroxy esters in high yields. Indium α-bromo enolates were also prepared and reacted with carbonyl compounds to give Darzens-type α,β-epoxy carbonyl products. © The Royal Society of Chemistry 2000.
DOI： 10.1039/a907334e
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Shuki ARAKI, Kaori YAMAMOTO, Tomoko INOUE, Koji FUJIMOTO, Hatsuo YAMAMURA, Masao KAWAI, Yasuo BUTSUGAN, Jinkui ZHOU, Emerich EICHHORN,Anton RIEKER, Martina HUBER
J. Chem. Soc., Perkin Trans. 2 985 - 995 1999年04月
掲載種別：研究論文（学術雑誌）
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Regioselective Allylation of Electron-deficient Alkenes with Organogallium and Organoindium Reagents 査読あり
Shuki ARAKI, Tomoaki HORIE, Motoshi KATO, Tsunehisa HIRASHITA, Hatsuo YAMAMURA, Masao KAWAI
Tetrahedron Lett. 40 2331 - 2334 1999年04月
掲載種別：研究論文（学術雑誌）
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Preparation of gamma-Heterosubstituted Allylindium and Diindium Reagents and Their Reactions with Carbonyl Compounds 査読あり
Tsunehisa HIRASHITA, Toshiya KAMEI, Tomoaki HORIE, Hatsuo YAMAMURA, Masao KAWAI, Shuki ARAKI
J. Org. Chem. 64 172 - 177 1999年04月
掲載種別：研究論文（学術雑誌）
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Preparation and Pproperties of Novel Gramicidin S Analogs Possessing a Tri-, Tetra- or Pentamethylene Bridge between Ornithine SideC.hains 査読あり
K. YAMADA, K. ANDO, Y. TAKAHASHI, Y. H. YAMAMURA, S. ARAKI, K. KOBAYASHI, R. KATAKAI, F. KATO, M. KAWAI
J. Peptide Res. 53 611 - 617 1999年04月
掲載種別：研究論文（学術雑誌）
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Hatsuo YAMAMURA, Shinichi YAMADA, Keiko KOHNO, Nozomi OKUDA, Shuki ARAKI, Kyoko KOBAYASHI, Ryoichi KATAKAI, Kazuaki KANO, MasaoKAWAI
J. Chem. Soc., Perkin Trans. 1 2943 - 2948 1999年04月
掲載種別：研究論文（学術雑誌）
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Hatsuo YAMAMURA, Daisuke Iida, Shuki ARAKI, Kyoko KOBAYASHI, Ryoichi KATAKAI, Kazuaki KANO, Masao KAWAI
J. Chem. Soc., Perkin Trans. 1 3111 - 3115 1999年04月
掲載種別：研究論文（学術雑誌）
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Photochemistry of Mesoionic Compounds. Photochemical Conversion of 5-Azido-1,3-diaryltetrazolium Aalts to Novel TricyclicMesoions with a Tetrazolo[1,5-a]benzimidazole Skelton 査読あり
Shuki ARAKI, Hiromi HATTORI, Noriyuki SHIMIZU, Koji OGAWA, Hatsuo YAMAMURA, Masao KAWAI
J. Heterocyclic Chem. 36 863 - 867 1999年04月
掲載種別：研究論文（学術雑誌）
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Optical Resolution and Absolute Configuration of N-Benzyloxycarbonyl-alpha-alkoxyglycines 査読あり
Masao KAWAI, Keiichi YAMADA, Kouji HOSODA, Yasuhiro OMORI, Shuji KATO, Nobuhiro NAGAYAMA, Seigo MASUI, Masao KAMIYA, HastuoYAMAMURA, Shuki ARAKI, Yasuo BUTSUGAN
Chirality 11 561 - 568 1999年04月
掲載種別：研究論文（学術雑誌）
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Convenient Preparation of [OrnTTfa]2- and [Orn(Boc)2,Orn(Tfa)2'] gramicidin S, Versatile Unsymmetrically Protected Derivatives ofGramicidin S 査読あり
K. YAMADA, K. ANDO, Y. TAKAHASHI, H. YAMAMURA, S. ARAKI, M. KAWAI
J. Peptide Res. 54 168 - 173 1999年04月
掲載種別：研究論文（学術雑誌）
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Chelation-controlled Regio- and Stereoselective Allylindation of Norbornenols 査読あり
Shuki ARAKI, Toshiya KAMEI, Yukimitsu IGARASHI, Tsunehisa HIRASHITA, Hatsuo YAMAMURA, Masao KAWAI
Tetrahedron Lett 40 7999 - 8002 1999年04月
掲載種別：研究論文（学術雑誌）
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Convenient preparation of [Orn(Tfa)2]- and [Orn(Boc)2, Orn(Tfa)2']gramicidin S, versatile unsymmetrically protected derivatives of gramicidin S 査読あり
K. Yamada, K. Ando, Y. Takahashi, H. Yamamura, S. Araki, M. Kawai
Journal of Peptide Research 54 ( 2 ) 168 - 173 1999年
記述言語：英語 掲載種別：研究論文（学術雑誌）
Treatment of gramicidin S (GS) with trifluoroacetic anhydride afforded a derivative in which only one of the two Orn side chains was trifluoroacetylated in 72% yield, furnishing the first efficient method for the preparation of a monoprotected derivative of GS. The mono(Tfa) derivative [Orn(Tfa)2]GS was treated with di-tert-butyl dicarbonate to yield dually protected derivative [Orn(Boc)2, Orn(Tfa)2']GS from which another monoprotected derivative [Orn(Boc)2]GS was prepared in high yield. These unsymmetrically protected GS derivatives are versatile starting materials for the preparation of various other GS derivatives. As an example of application of the unsymmetrically protected derivatives, a dimeric GS derivative was prepared via a singly p-nitrobenzenesulfonyl(NBS)-activated derivative [Orn(Boc)2,Orn(NBS)2']GS.
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Synthesis, electrochemical investigation and EPR spectroscopy of a reversible four-stage redox system based on mesoionic 5,5'-azinobis(1,3-diphenyltetrazole) and related mesoionic compounds 査読あり
Shuki Araki, Kaori Yamamoto, Tomoko Inoue, Koji Fujimoto, Hatsuo Yamamura, Masao Kawai, Yasuo Butsugan, Jinkui Zhou, Emerich Eichhorn, Anton Rieker, Martina Huber
Journal of the Chemical Society. Perkin Transactions 2 ( 5 ) 985 - 995 1999年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Royal Society of Chemistry
Mesoionic 5,5'-azinobis(1,3-diphenyltetrazole) 1 was prepared, and its chemical oxidation gave stable crystals of the corresponding radical cation 1.+ and dication 12+, which reversibly gave back azine 1 on reduction with zinc. Electrochemical investigations of 1 using cyclovoltammetry and differential pulse voltammetry in pyridine (Py) or dichloromethane (DCM) also revealed the two reversible successive one-electron oxidations leading to dication 12+ via radical cation 1.+, both of which can be reduced to the neutral state 1. In the cathodic process, 1 was reduced by two consecutive one-electron transfers at only slightly different potentials up to the corresponding diamon 12- which could be re-oxidized to the neutral state
thus constituting a reversible four-stage redox system. Radical cation 1.+ and anion 1.- were characterized by EPR spectroscopy. In order to get more insights into the spin-density distribution of 1.+, the bis- and tetra-15N-labelled species 1a.+, 1b.+ and 1c.+ were synthesized and investigated by EPR and 15N as well as 14N ENDOR spectroscopy, revealing that the largest N hyperfine coupling constants are due to the nitrogen atoms of the central bridge. According to 1H ENDOR there seems to be a small coupling with the protons of both phenyl rings which cannot be resolved in the EPR spectrum. The electrochemical properties of the related mesoionic compounds 5-10 were also investigated in Py or DCM solutions. In the cathodic process, a reduction peak of 9 and 10 was observed due to their reversible one-electron reduction to the corresponding radical anions. The radical obtained on reduction of 10 was characterized by EPR spectroscopy. On the other hand, 5-8 can be reduced by a formal two-electron transfer up to the corresponding dianions which are re-oxidizable to the neutral state. In the anodic process, 9/10 undergo irreversible one-electron oxidations whereas 5/6 (in DCM) and 7/8 (in Py) experience reversible or irreversible step by step two-electron oxidations leading to the dications. In Py the oxidation products of 5/6 react to further species revealing two more oxidation and several rereduction peaks. On the other hand, the oxidation products of 7/8 are instable in DCM (one main oxidation and rereduction peak). The electrochemical data are discussed in terms of delocalization in the cations and conjugation in the dications.DOI： 10.1039/a809386e
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Preparation and properties of novel gramicidin S analogs possessing a tri-, tetra- or pentamethylene bridge between ornithine side chains 査読あり
K. Yamada, K. Ando, Y. Takahashi, Y. Oda, H. Yamamura, S. Araki, K. Kobayashi, R. Katakai, F. Kato, Masao Kawai
Journal of Peptide Research 53 ( 6 ) 611 - 617 1999年
記述言語：英語 掲載種別：研究論文（学術雑誌）
Gramicidin S (GS) analogs in which the N(δ) atoms of the two Orn side chains are linked by an oligomethylene bridge [-(CH2)(n)-
n=3-5] were prepared via the bis(p-nitrobenzenesulfonyl) derivative [Orn(NBS)(2,2')]GS. For comparison the nonbridged secondary amino group-containing analog [Orn(ME)(2,2')]GS was also prepared. 1H NMR and CD spectral analysis indicated that these analogs adopt the same β-sheet conformation as GS. The antimicrobial activities of these analogs were very similar, but were slightly dependent on the bridge chain length, the trimethylene-bridge analog being the most potent. -
Preparation and properties of novel gramicidin S analogs possessing a polymethylene bridge between ornithine side chains 査読あり
K Yamada, K Ando, Y Takahashi, H Yamamura, S Araki, M Kawai
PEPTIDE SCIENCE - PRESENT AND FUTURE 775 - 776 1999年
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Preparation and guest binding of novel β-cyclodextrin dimers linked with various sulfur-containing linker moieties t 査読あり
Hatsuo Yamamura, Shinichi Yamada, Keiko Kohno, Nozomi Okuda, Shuki Araki, Kyoko Kobayashi, Ryoichi Katakai, Kazuaki Kano, Masao Kawai
Journal of the Chemical Society - Perkin Transactions 1 ( 20 ) 2943 - 2948 1999年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Royal Society of Chemistry
Novel cyclodextrin dimers (1, 2, 3 and 4) whose cyclodextrins were linked with sulfur-containing linkers, namely a thiodipropanamide, a dithiodipropanamide, a thiodiethanamide, or a dithiodiethanamide linker, were synthesized by a reaction of 6-amino-6-deoxycycIoheptaose 7 with the corresponding dicarboxylic acids. For their preparation, dicyclohexylcarbodiimide, l-(3-dimethylaminopropyl)-3-ethylcarbodiimideand(benzotriazol-l-yloxy) tripyrroIidinophosphonium hexafluorophosphate were examined as coupling reagents. 'H NMR studies of the dimers suggested an intramolecular inclusion of the linker moiety to the cyclodextrin cavity, which affected the complexation of guest molecules. Dimer 4 was converted to another type of dimer 5 by reductive cleavage of the disulfide bond to generate thiol group-containing mononieric species followed by a substitution reaction with 6-O-tosyl derivative 6. © The Royal Society of Chemistry 1999.
DOI： 10.1039/a905067a
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Polysulfonylated cyclodextrins. Part II.1 Preparation and structural validation of three isomeric pentakis(6-0-mesitylsulfonyl)cyclomaltoheptaoses f 査読あり
Hatsuo Yamamura, Daisuke Lida, Shuki Araki, Kyoko Kobayashi, Ryoichi Katakai
Journal of the Chemical Society - Perkin Transactions 1 ( 21 ) 3111 - 3115 1999年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Royal Society of Chemistry
Three isomers of cyclomaltoheptaose derivatives, la-c, which possess five mesitylenesulfonyloxy groups on their C-6 atoms, were prepared. Assignment of the regiosiomers was performed by their conversion into compounds containing five 3,6-anhydroglucose units followed by 'H NMR analyses. The structures of the pentakis(3,6-anhydro) derivatives were also confirmed by their derivation from the known bis(TBDMS) derivatives. ©The Royal Society of Chemistry 1999.
DOI： 10.1039/a906436b
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Photochemistry of mesoionic compounds. Photochemical conversion of 5-azido-1,3-diaryltetrazolium salts to novel tricyclic mesoions with a tetrazolo[1,5-a]benzimidazole skeleton 査読あり
Shuki Araki, Hiromi Hattori, Noriyuki Shimizu, Koji Ogawa, Hatsuo Yamamura, Masao Kawai
Journal of Heterocyclic Chemistry 36 ( 4 ) 863 - 867 1999年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：HeteroCorporation
A new type of tetrazolium-5-amide mesoions 2 with a tricyclic tetrazolo[1,5-a]benzimidazole skeleton has been synthesized via photolysis of 5-azido-1,3-diaryltetrazolium salts 1.
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Optical resolution and absolute configuration of N-benzyloxycarbonyl-alpha-alkoxyglycines 査読あり
M Kawai, K Yamada, K Hosoda, Y Omori, S Kato, N Nagayama, S Masui, M Kamiya, H Yamamura, S Araki, Y Butsugan
CHIRALITY 11 ( 7 ) 561 - 568 1999年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：WILEY-LISS
Optical resolution of racemic N-benzyloxycarbonyl-protected alpha-alkoxy-glycines, (+/-)-Cbz-Gly(OR)-OH (R = Et and Pr-2), was achieved by means of fractional crystallization of diastereomeric salts with (+)-(1S,2S)-2-amino-1-phenyl-1,3-propanediol or diastereomeric esters of (+)- or (-)-menthol. The D- and L-configurations were assigned to the (+)- and (-)-Cbz-Gly(OR)-OH, respectively, based on L-enantioselective enzymatic hydrolysis of (+/-)-Cbz-Gly(OR)-OR' (R = Me, Et, and Pr-i; R' = CH2CF3 and Me) using porcine pancreatic lipase and papain. Chiroptical properties and HPLC retention times of D- and L-Gly(OR)-residue (R = Me and Pr-i)-containing peptides were compared in relation to their configurational assignments. (C) 1999 Wiley-Liss, Inc.
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Stereodivergent Allylindation of Cyclopropenes. Remarkable Stereodirection and Aaceleration by Neighbouring Carboxyl and HydroxylGroups 査読あり
Shuki ARAKI, Hiroyuki NAKANO, Kandasamy SUBBURAJ, Syunehisa HIRASHITA, Kensuke SHIBUTANI, Hastuo YAMAMURA, Masao KAWAI, YasuoBUTSUGAN
Tetrahedron Lett 39 6327 - 6330 1998年04月
掲載種別：研究論文（学術雑誌）
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Stereochemistry of Protected Ornithine Side Chains in Gramicidin D Derivatives and Their Resistance to N-Methylation 査読あり
Masao KAWAI, Tatsuo YAMAMOTO, Keiichi YAMADA, Masashi YAMAGUCHI, Shigehiro KUROBE, Hastuo YAMAMURA, Shuki ARAKI, Yasuo BUTSUGAN,Kyoko KOBAYASHI, Ryoichi KATAKAI, Kazuki SAITO, Terumi NAKAJIMA
Lett. Pept. Sci. 5 5 - 12 1998年04月
掲載種別：研究論文（学術雑誌）
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Hastuo YAMAMURA, Tadahiro YOTSUYA, Satoshi USAMI, Akihito IWASA, Shoji ONO, Yoshihisa TANABE, Daisuke IIDA, Takao KATSUHARA, KazuakiKANO, Testuo UCHIDA, Shuki ARAKI, Masao KAWAI
J. Chem. Soc., Perkin Trans. 1 1299 - 1303 1998年04月
掲載種別：研究論文（学術雑誌）
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Keiichi YAMADA, Hirotaka OZAKI, Naoki KANDAa, Hastuo YAMAMURA, Shuki Araki, Masao KAWAI
J. Chem. Soc., Perkin Trans. 1 3999 - 4004 1998年04月
掲載種別：研究論文（学術雑誌）
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Nitrogen-rich Mesoionic Compounds from 5-Chloro-1,3-diaryltetraazolium Salts and Nitrogen Nucleophiles. Synthesisand Properties of 5-Azido-1,3-diaryltetrazolium Salts 査読あり
Shuki ARAKI, Kaori YAMAMOTO, Misako YAGI, Tomoko INOUE, Hiroyo FUKUNAGA, Hiromi HATTORI, Hastuo YAMAMURA, Masao KAWAI, YasuoBUTSUGAN
Eur. J. Org. Chem. 121 - 127 1998年04月
掲載種別：研究論文（学術雑誌）
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Primary hydroxy-modified cyclomaltoheptaose derivatives with two kinds of substituents. Preparation of 6(I)-(benzyloxycarbonylamino)-, 6(I)-(tert-butoxycarbonylamino)- and 6(I)-azido-6(I)-deoxy-6(II),6(III),6(IV),6(V),6(VI),6(VII)-hexa-O-tosylcyclomaltoheptaose and their conversion to the hexakis-(3,6-anyhdro) derivatives 査読あり
H Yamamura, T Yotsuya, S Usami, A Iwasa, S Ono, Y Tanabe, D Iida, T Katsuhara, K Kano, T Uchida, S Araki, M Kawai
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 ( 7 ) 1299 - 1303 1998年04月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：ROYAL SOC CHEMISTRY
Three cyclomaltoheptaoses (1, 2 and 3) which possess a benzyloxycarbonylamino group, a tert-butoxycarbonylamino group or an azido group, and six tosyloxy groups, on their C-6 atoms have been prepared. These can be versatile intermediates for the synthesis of derivatives possessing an amino group as well as other functional groups. As an example of their derivatization, their conversion to compounds containing 3,6-anhydroglucoses, which possess cation-binding abilities, is also reported.
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Stereochemistry of protected ornithine side chains in gramicidin S derivatives and their resistance to N-methylation 査読あり
Masao Kawai, Tatsuo Yamamoto, Keiichi Yamada, Masashi Yamaguchi, Shigehiro Kurobe, Hatsuo Yamamura, Shuki Araki, Yasuo Butsugan, Kyoko Kobayashi, Ryoichi Katakai, Kazuki Saito, Terumi Nakajima
Letters in Peptide Science 5 ( 1 ) 5 - 12 1998年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Springer Netherlands
Derivatives of gramicidin S (GS) and its mono- and di-D-cyclohexylalanine (D-Cha) analogs possessing various protecting groups on Orn side chains were prepared. 1H NMR spectra of the unsymmetrically protected analogs [Orn(X)2,Orn(X′)2′,D-Cha4]GS were similar to the composites of the spectra of the symmetrical derivatives [Orn(X)2,2′,D-Cha4,4′]GS and [Orn(X′)2,2′]GS, revealing the proximity of the protecting groups of NδH of Orn residues at the 2 and 2′ positions to the side chains of D-Phe (or D-Cha) residues at the 4 and 4′ positions, respectively. The results indicated the presence of H-bonds between the NδH of Orn and the carbonyl of D-Phe residues in the i → i + 2 sense and not in i → i - 3, which was also supported by the ROESY analysis. The substantially strong H-bonds can explain the observed resistance of the urethane NH of the Orn side chains in the GS derivatives to the N-methylation with CH3I-Ag2O in DMF.
DOI： 10.1007/BF02443534
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Selective Reduction of Organic Functional Groups with Indium Hydride Reagents 査読あり
Masafumi YAMADA, Koji TANAKA, Yasuo BUTSUGAN, Masao KAWAI, Hastuo YAMAMURA, Shuki ARAKI
Main Group Metal Chemistry 20 ( 4 ) 241 - 246 1997年04月
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High gamma-Selectivity in the Coupling of Penta-2,4-dienyl- and Pent-2-en-4-ynylindium Reagents with Aldehy 査読あり
Tsunehisa HIRASHITA, Shi'ichiro INOUE, Hastuo YAMAMURA, Masao KAWAI, Shuki ARAKI
J. Organometalic Chemistry 549 305 - 309 1997年04月
掲載種別：研究論文（学術雑誌）
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Diastereoselective Reduction of Acyclic Hydroxyketones and Diketones with an Indium Hydride Reagent 査読あり
Masafumi YAMADA, Tomoaki Horie, Masao KAWAI, Hastuo YAMAMURA, Shuki ARAKI
Tetrahedron 53 15685 - 15690 1997年04月
掲載種別：研究論文（学術雑誌）
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Convenient Enantioselective Preparation of Salsolinol-1-carboxylic Acid 査読あり
Masao KAWAI, Yulin Deng, Ikuko KIMURA, Hatsuo YAMAMURA, Shuki ARAKI, Makoto NAOI
Tetrahedron: Asymmetry 8 1487 - 1490 1997年04月
掲載種別：研究論文（学術雑誌）
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Assay for the (R)- and (S)-Enantiomers of Salsolinols in Biological Samples and Foods with Ion-pair High-performance liquidChromatography using beta-Cyclodextrin as a Chiral mobile Phase Additive 査読あり
Yulin Deng, Wakako MARUYAMA, Masao KAWAI, Philippe Dostert, Hatsuo YAMAMURA, Tsutomu TAKAHASHI, Makoto NAOI
J. Chromatography B. 689 313 - 320 1997年04月
掲載種別：研究論文（学術雑誌）
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Assay for the (R)- and (S)-Enantiomers of Salsolinols in Biological Samples and Foods with Ion-pair High-performance liquidChromatography using beta-Cyclodextrin as a Chiral mobile Phase Additive 査読あり
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J. Chromatography B. 689 313 - 320 1997年04月
掲載種別：研究論文（学術雑誌）
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Selective reduction of organic functional groups with indium hydride reagents 査読あり
Masafumi Yamada, Koji Tanaka, Yasuo Butsugan, Masao Kawai, Hatsuo Yamamura, Shuki Araki
Main Group Metal Chemistry 20 ( 4 ) 241 - 246 1997年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Walter de Gruyter GmbH
New indium hydride reagents LiPhnInH4-n (n = 0-2) were prepared and their reactivity and selectivity for various organic compounds containing representative functional groups were studied. It was shown that the reactivity can be controlled by changing the substituents and their number on the central indium atom. Their stereoselectivities were comparable to those of sodium borohydride and lithium aluminium hydride.
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Mechanism of enantioseparation of salsolinols, endogenous neurotoxins in human brain, with ion-pair chromatography using beta-cyclodextrin as a mobile phase additive 査読あり
YL Deng, W Maruyama, H Yamamura, M Kawai, P Dostert, M Naoi
ANALYTICAL CHEMISTRY 68 ( 17 ) 2826 - 2831 1996年09月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：AMER CHEMICAL SOC
A novel method for direct separation of the enantiomers of salsolinol and N-methylsalsolinol was devised, The enantiomers were completely separated with ion-pair chromatography on a reversed-phase column with beta-cyclodextrin as a chiral mobile phase additive and sodium 1-heptanesulfonate as a counterion. The mechanism for enantioseparation with this ion-pair system containing a-cyclodextrin was discussed, The effects of beta-cyclodextrin, counterions, pH, ionic strength, and organic solvent on retention were investigated, and a retention model was proposed and proved to be consistent with the experimental data. A preliminary study of the enantiomeric composition of salsolinol and N-methylsalsolinol in banana and in human brain was made as an example of the application of this assay.
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Structural Revision of Physalin H Isolated from Physalis anguluta 査読あり
Bunsho MAKINO, Masao KAWAI, Toichi OGURA, Masaki NAKANISHI, Hatsuo YAMAMURA, Yasuo BUSTUGAN
J. Natural Products 58 1668 - 74 1996年04月
掲載種別：研究論文（学術雑誌）
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Preparation of Protected alpha-Alkoxyglycines. 査読あり
Masao KAWAI, Kouji HOSODA, Yoshimasa Omori, Keiichi YAMADA, Shiko HAYAKAWA, Hatsuo YAMAMURA, Yasuo BUSTUGAN
Synthetic Communications 26 1545 - 1554 1996年04月
掲載種別：研究論文（学術雑誌）
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Mechanism of Enantioseparation of Salsolinols, Endogenous Neurotoxins in Human Brain, with Ion-Pair Chromatography Usingbeta-Cyclodextrin as a Mobile Phase Additive. 査読あり
Yulin Deng, Wakako MARUYAMA, Hatsuo YAMAMURA, Masao KAWAI, Philippe Dostert, Makoto NAOI
Anal. Chem. 68 2826 - 2831 1996年04月
掲載種別：研究論文（学術雑誌）
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Indium-mediated Reaction of 1,3-Dichloro- and 1,3-Dibromopropens with Carbonyl Compounds. Generation of Novel 3,3-Diindiopropene. 査読あり
Shuki ARAKI, Tsunehisa HIRASHITA, Hidetaka SHIMIZU, Hatsuo YAMAMURA, Masao KAWAI, Yasuo BUTSUGAN
Tetrahedron Lett. 37 8417 - 8420 1996年04月
掲載種別：研究論文（学術雑誌）
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Dependence of Guest-binding Ability on Cavity Shape of Deformed Cyclodextrins. 査読あり
Kahee FUJITA, Yuji OKABE, Kazuko OHTA, Hatsuo YAMAMURA, Tsutomu TAHARA, Yasuyoshi NOGAMI, Toshitaka KOGA
Tetrahedron Lett. 37 1825 - 1828 1996年04月
掲載種別：研究論文（学術雑誌）
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A Cyclodextrin Derivative with Cation Carrying Ability: Heptakis(3,6-anhydro)-beta-cyclodextrin 2-O-p-Phenylazobenzoate. 査読あり
Hatsuo YAMAMURA, Hirotake KAWAI, Tadahiro YOTSUYA, Tamotsu HIGUCHI, Yasuo BUTSUGAN, Shuki ARAKI, Masao KAWAI, Kahee FUJITA
Chem. Lett. 799 - 780 1996年04月
掲載種別：研究論文（学術雑誌）
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Hatsuo YAMAMURA, Hideki MASUDA, Yoshitaka KAWASE, Masao KAWAI, Yasuo BUTSUGAN, Hisahiko EINAGA
J. Chem. Soc., Chem. Commun. 1069 - 1079 1996年04月
掲載種別：研究論文（学術雑誌）
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Upon 'Physalin L' Isolated from Physalis minima 査読あり
Masao KAWAI, Bunsho MAKINO, Hatsuo YAMAMURA, Yasuo BUTSUGAN
Phytochemistry 43 661 - 663 1996年04月
掲載種別：研究論文（学術雑誌）
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A cyclodextrin derivative with cation carrying ability: Heptakis(3,6-anhydro)-beta-cyclodextrin 2-O-p-phenylazobenzoate 査読あり
H Yamamura, H Kawai, T Yotsuya, T Higuchi, Y Butsugan, S Araki, M Kawai, K Fujita
CHEMISTRY LETTERS ( 9 ) 799 - 800 1996年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：CHEMICAL SOC JAPAN
A cation-complexing host, heptakis(3,6-anhydro)-beta-cyclodextrin, was converted to a mono-p-phenylazobenzoyl derivative, which exhibited alkali metal-carrying ability in CH2Cl2-H2O system.
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X-Ray crystallographic study of octakis(3,6-anhydro)-γ-cyclodextrin with a highly specific cation binding ability 査読あり
Hatsuo Yamamura, Hideki Masuda, Yoshitaka Kawase, Masao Kawai, Yasuo Butsugan, Hisahiko Einaga
Chemical Communications ( 9 ) 1069 - 1070 1996年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Royal Society of Chemistry
Octakis(3,6-anhydro)-γ-cyclodextrin, which is composed of eight 3,6-anhydroglucoses, is analysed by X-ray crystallography to determine its unique structure which contains a hydrophilic cavity enabling specific binding to Cs+.
DOI： 10.1039/CC9960001069
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Upon 'physalin L' isolated from Physalis minima 査読あり
Masao Kawai, Bunsho Makino, Hatsuo Yamamura, Yasuo Butsugan
Phytochemistry 43 ( 3 ) 661 - 663 1996年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Elsevier Ltd
5α-Ethoxy-6β-hydroxy- and 6β-ethoxy-5α-hydroxy-5,6-dihydrophysalin B were derived from the corresponding 5β,6β- and 5α,6α-epoxides, respectively, by acid treatment in ethanol. The 5α-ethoxy derivative was isolated as an artefact from Physalis alkekengi, while other workers isolated the 6β-ethoxy compound as a constituent of P. minima and mistakenly named it as physalin L, which had already been assigned to (25S)-3,4-didehydro- 2,3,25,27-tetrahydrophysalin A. The 1H NMR spectrum of the 6β-ethoxy derivative prepared by us, however, did not agree with the reported data.
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Studies on the construction of allosteric model peptides carrying beta-cyclodextrin and picolylamino or picolynylamino group 査読あり
H Yamamura, M Kawai, R Hirasawa, K Yamada, Y Butsugan
PEPTIDE CHEMISTRY 1995 533 - 536 1996年
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Preparation of protected alpha-alkoxyglycines 査読あり
M Kawai, K Hosoda, Y Omori, K Yamada, S Hayakawa, H Yamamura, Y Butsugan
SYNTHETIC COMMUNICATIONS 26 ( 8 ) 1545 - 1554 1996年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：MARCEL DEKKER INC
N-Carbobenzoxy-alpha-alkoxyglycine esters were synthesized by H2SO4-catalyzed O-alkylation of N-carbobenzoxy-alpha-hydroxyglycine and also by base treatment of N-carbobenzoxy-N-chloroglycine methyl ester in the corresponding alcohol. Saponification of the protected alpha-alkoxyglycines gave free acids which can be used for the synthesis of alpha-alkoxyglycine residue-containing peptides.
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2 ALTERNATIVE CONFORMATIONAL STATES OF ALPHA,ALPHA-DIALKYLGLYCYL-L-PROLYL SEQUENCES GOVERNED BY PRESENCE ABSENCE OF AN NH GROUP DIRECTLY FOLLOWING THE PROLINE RESIDUE, X-RAY CRYSTAL AND MOLECULAR-STRUCTURES OF BOC-D-IVA-L-PRO-NHBZL AND BOC-L-IVA-PRO-NHBZL 査読あり
M KAWAI, Y OMORI, H YAMAMURA, Y BUTSUGAN, T TAGA, Y MIWA
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 ( 17 ) 2115 - 2122 1995年09月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：ROYAL SOC CHEMISTRY
The crystal structures of the isovaline-containing dipeptides, Boc-D-Iva-L-Pro-NHBzl 4 and Boc-L-Iva-L-Pro-NHBzl 5 were determined by X-ray diffraction. The diastereoisomeric peptides adopt intramolecular hydrogen-bonded beta-turn conformations closely similar to each other (4:phi(Iva) -51 degrees, psi(Iva) -38 degrees, phi(Pro) - 70 degrees and psi(Pro) -17 degrees and 5:phi(Iva) -53 degrees, psi(Iva) -35 degrees, phi(Pro) -72 degrees and psi(Pro) -14 degrees). The Pro ring of each peptide is in CY-exo conformation. These conformations are essentially the same as those in the reported crystal structures of the Aib-L-Pro sequence possessing an NH group directly attached to the carbonyl of the L-Pro, indicating that replacement of either one of the two methyl groups of the Aib moiety with an ethyl group does not cause any significant change in the beta-turn conformation of the Aib-L-Pro sequence in the crystalline state.
CD spectral analysis of the terminal chromophoric group-carrying peptides Dnp-Gly-X-L-Pro-Gly-pNA (X = Aib 6 and D/L-Iva 7/8) has shown that these three tetrapeptides in CHCl3 and THF solutions also adopt a beta-turn-type conformation. CD spectra of glycolic acid residue-containing analogues in place of the fourth Gly residue revealed a lack of beta-turn tendency in these analogues, indicating the importance of intramolecular hydrogen bonding for the beta-turn conformation of the central dipeptide moieties. The results are consistent with the reported unturned crystal structures of Aib-L-Pro and D/L-Iva-L-Pro sequence-containing peptides tacking the NH group which directly follows the Pro residue available for intramolecular hydrogen bonding. -
Masao KAWAI, Yoshimasa OMORI, Hatsuo YAMAMURA, Yasuo BUSTUGAN, Yoshihisa MIWA
J. Chem. Soc. Perkin Trans. 1 2115 - 2122 1995年04月
掲載種別：研究論文（学術雑誌）
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Synthesis of a 'Head-to-tail' Type Cyclodextrin Dimer Linked by a Disulfide Bridge 査読あり
Yuji OKABE, Hatsuo YAMAMURA, Kei-ichi OBE, Kazuko OHTA, Masao KAWAI, Kahee FUJITA
J. Chem. Soc., Chem. Commun. 581 - 582 1995年04月
掲載種別：研究論文（学術雑誌）
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Synthesis and Alkali Metal Ion Binding of Poly(3,6-anhydro)-alpha-cyclodextrins 査読あり
Hatsuo YAMAMURA, Hideki NAGAOKA, Masao KAWAI, Yasuo BUTSUGAN, Kahee FUJITA
Tetrahedron Lett. 36 1093 - 1094 1995年04月
掲載種別：研究論文（学術雑誌）
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Structural Revision of Physalin H Isolated from Physalis anguluta 査読あり
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J. Natural Products 58 1668 - 74 1995年04月
掲載種別：研究論文（学術雑誌）
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Physalins Possessing an Endoperoxy Structure from Physalis Alkekengi var. francheti. Structural Revision of Physalin K. 査読あり
Busho MAKINO, Masao KAWAI, Yasushi IWATA, Hatsuo YAMAMURA, Yasuo BUTSUGAN, Kiyoshi OGAWA, Mitsuo HAYASHI
Bull. Chem. Soc. Jpn. 68 219 - 226 1995年04月
掲載種別：研究論文（学術雑誌）
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New Physalins Possessing an Additional Carbon-carbon-bond from Physalis alkekengi var. francheti. 査読あり
Bunsho MAKINO, Masao KAWAI, Koji KITO, Hatsuo YAMAMURA, Yasuo BUSTUGAN
Tetrahedron 51 12529 - 12538 1995年04月
掲載種別：研究論文（学術雑誌）
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PHYSALINS POSSESSING AN ENDOPEROXY STRUCTURE FROM PHYSALIS-ALKEKENGI VAR FRANCHETI - STRUCTURAL REVISION OF PHYSALIN-K 査読あり
B MAKINO, M KAWAI, Y IWATA, H YAMAMURA, Y BUTSUGAN, K OGAWA, M HAYASHI
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 68 ( 1 ) 219 - 226 1995年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：CHEMICAL SOC JAPAN
Physalin K was isolated from Physalis alkekengi var. francheti. Spectroscopic studies and chemical correlations, however, revealed that the reported structure of physalin K at the AB ring moiety, namely, 4 alpha,5 alpha-epoxy-6 alpha-hydroxy-2-en-1-one, should be revised to 2 alpha,5 alpha-epidioxy-6 beta-hydroxy-3-en-1-one. A new physalin,named physalin Q, was also isolated and identified as the 2 beta,5 beta-epidioxy diastereomer of physalin K.
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Synthesis of a 'head-to-tail' type cyclodextrin dimer linked by a disulfide bridge 査読あり
Yuji Okabe, Hatsuo Yamamura, Ken-Ichi Obe, Kazuko Ohta, Masao Kawai, Kahee Fujita
Journal of the Chemical Society, Chemical Communications ( 5 ) 581 - 582 1995年
記述言語：英語 掲載種別：研究論文（学術雑誌）
A 'head-to-tail' type cyclodextrin dimer, where C-3 of one cyclodextrin and C-6 of the other are linked by a disulfide bond, is synthesized using 2,2′-dipyridyl disulfide, which is widely applicable to the preparation of other dimers.
DOI： 10.1039/C39950000581
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Crystal Structures of 5a,6a-Epoxy and 2,3-Dihydro Derivatives of Physalin B, a 13,14-seco-16,24-Cyclosteroid, and Their 1HNMR SpectralAnalysis 査読あり
Masao KAWAI, Bunsho MAKINO, Tooru TAGA, Yoshihisa MIWA, Tatsuo YAMAMOTO, Tsunehiro FURUTA, Hatsuo YAMAMURA, Yasuo BUTSUGAN, KiyoshiOGAWA, Mitsuo HAYASHI
Bull. Chem. Soc. Jpn. 67 222 - 226 1994年04月
掲載種別：研究論文（学術雑誌）
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Crystal structures of 5α,6α-epoxy and 2,3-dihydro derivatives of physalin B, a 13,14-seco-16,24-cyclosteroid, and their 1H NMR spectral analysis 査読あり
M. Kawai, B. Makino, T. Taga, Y. Miwa, T. Yamamoto, T. Furuta, H. Yamamura, Y. Butsugan, K. Ogawa, M. Hayashi
Bulletin of the Chemical Society of Japan 67 ( 1 ) 222 - 226 1994年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Chemical Society of Japan
X-Ray crystallographic analysis of two steroid derivatives, 5α,6α-epoxyphysalin B and 2,3-dihydrophysalin B, have been undertaken, revealing their closely similar crystal structures to each other. Their 1H NMR spectra, as well as that of the parent compound physalin B, a 13,14-seco-16,24-cyclosteroid from Physalis alkekengi, have been analyzed based on the crystal structures of these derivatives.
DOI： 10.1246/bcsj.67.222
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CRYSTAL-STRUCTURES OF BOC-D-PRO-OBZL AND L-IVA-L-PRO-OBZL - UNTURNED CONFORMATION OF AIB-PRO SEQUENCE UNAFFECTED BY REPLACEMENT OF ME WITH ET IN AIB 査読あり
M KAWAI, Y OMORI, H YAMAMURA, Y BUTSUGAN, T TAGA, Y MIWA
BIOPOLYMERS 33 ( 8 ) 1207 - 1212 1993年08月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：JOHN WILEY & SONS INC
The crystal structures of the isovaline (Iva) containing dipeptides, Boc-D-Iva-L-Pro-OBzl and Boc-L-Iva-L-Pro-OBzl, were determined by x-ray diffraction. The diastereomeric peptides were shown to adopt unturned conformations closely similar to each other (phi(Iva) 52-degrees, psi(Iva) 46-degrees, phi(Pro) -65-degrees, and phi(Pro) 143-degrees for D-Iva-L-Pro sequence and phi(Iva) 52-degrees, ps(Iva) 44-degrees, phi(Pro) -63-degrees, and psi(Pro) 148-degrees for L-IVa-L-Pro sequence). The Pro ring of each peptide was in C(gamma)-endo conformation. The unusually large angle C(Iva)-N(Pro)-C(Pro)delta values (131-degrees in both peptides) were observed, that was due to steric repulsion between the delta-methylene of Pro and the alkyl side chain of Iva residue. These conformations were essentially the same as that of the corresponding alpha-aminoisobutyric acid (Aib) -containing peptide Boc-Aib-L-Pro-OBzl. The result has demonstrated that replacement of either one of the two methyl groups of the Aib residue in Boc-Aib-L-Pro-OBzl with an ethyl group does not cause any significant change in the unturned conformation of the dipeptide. (C) 1993 John Wiley & Sons, Inc.
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Preparation of Polytosylated gamma-Cyclodextrins. 査読あり
Hatsuo YAMAMURA, Yoshitaka KAWASE, Masao KAWAI, Yasuo BUTSUGAN
Bull. Chem. Soc. Jpn. 66 ( 2 ) 585 - 588 1993年04月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：The Chemical Society of Japan
Practical preparation of polytosylated <i>γ</i>-cyclodextrins, octakis(6-<i>O</i>-tosyl)-2-<i>O</i>-tosyl-<i>γ</i>-cyclodextrin, octakis(6-<i>O</i>-tosyl)-<i>γ</i>-cyclodextrin, and heptakis(6-<i>O</i>-tosyl)-<i>γ</i>-cyclodextrin, has been established. The procedure involves reaction of <i>γ</i>-cyclodextrin with tosyl chloride in pyridine and column chromatographic separation using silica gel modified with 3-aminopropyl groups.
DOI： 10.1246/bcsj.66.585
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Hatsuo YAMAMURA, Toshishige EZUKA, Yoshitaka KAWASE, Masao KAWAI, Yasuo BUTSUGAN, Kahee FUJITA
J. Chem. Soc., Chem. Commun. ( 7 ) 636 - 637 1993年04月
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Determination of the Structures of Tris(6-O-mesitylenesulfonyl)-alpha-cyclodextrin Regioisomers by 1H NMRAnalyses of the Corresponding 3,6-Anhydrocyclodextrin Derivatives. 査読あり
Hatsuo YAMAMURA, Hideki NAGAOKA, Kazuki SAITO, Masao KAWAI, Yasuo BUTSUGAN
J. Org. Chem. 58 2936 - 2937 1993年04月
掲載種別：研究論文（学術雑誌）
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Crystal Structures of Boc-D- and L-Iva-L-Pro-OBzl: Unturned Conformation of Aib-Pro Sequence Unaffected by Replacement of Me with Et inAib 査読あり
Masao KAWAI, Toshihisa OMORI, Hatsuo YAMAMURA, Yasuo BUTSUGAN, Tooru TAGA, Yoshihisa MIWA
Biopolymers 33 1207 - 1212 1993年04月
掲載種別：研究論文（学術雑誌）
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Determination of the Structures of Tris(6-O-mesitylenesulfonyl)-α-cyclodextrin Regioisomers by 1H NMR Analyses of the Corresponding 3,6-Anhydrocyclodextrin Derivatives 査読あり
Hatsuo Yamamura, Hideki Nagaoka, Kazuki Saito, Masao Kawai, Yasuo Butsugan, Terumi Nakajima, Kahee Fujita
Journal of Organic Chemistry 58 ( 11 ) 2936 - 2937 1993年
記述言語：英語 掲載種別：研究論文（学術雑誌）
The structures of two regioisomers of tris(6-O-mesitylenesulfonyl)-α-cyclodextrin (6A,6B,6D and 6A,6B,6E) were assigned by conversion of the isomers to tris(3,6-anhydro)-α-cyclodextrins and analyses of the two-dimensional 1H NMR spectra (DQF-COSY, HOHAHA, and ROESY) of the anhydrocyclodextrins. © 1993, American Chemical Society. All rights reserved.
DOI： 10.1021/jo00063a005
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Selective Preparation of Hexakis(6-O-arenesulfonyl)-alpha-cyclodextrin 査読あり
Kahee FUJITA, Kazuko OHTA, Kozo MASUNARI, Ken-ichi OBE, Hatsuo YAMAMURA
Tetrahedron Lett. 33 5519 - 5520 1992年04月
掲載種別：研究論文（学術雑誌）
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Physalins N and O from Physalis Alkekengi. 査読あり
Masao KAWAI, Toichi OGURA, Bunsho MAKINO, Akihide MATSUMOTO, Hatsuo YAMAMURA, Yasuo BUTSUGAN, Mitsuo HAYASHI
Phytochemistry 31 4299 - 4302 1992年04月
掲載種別：研究論文（学術雑誌）
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Optical Resolution of N-Carbobenzoxy-alpha-methoxyglycine. 査読あり
Masao KAWAI, Yoshimasa OMORI, Hatsuo YAMAMURA, Yasuo BUTSUGAN
Tetrahedron: Asymmetry 8 1019 - 1020 1992年04月
掲載種別：研究論文（学術雑誌）
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Bunsho MAKINO, Masao KAWAI, Tatsuo YAMAMOTO, Hatsuo YAMAMURA, Yasuo BUTSUGAN, Mitsuo HAYASHI, Kiyoshi OGAWA
J. Chem. Soc., Chem. Commun. 1430 - 1431 1992年04月
掲載種別：研究論文（学術雑誌）
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A Complete Set of 6A-Azido-6A-deoxy-6X-O-sulfonyl- beta-cyclodextrins. 査読あり
Kahee FUJITA, Hatsuo YAMAMURA, Yoshimitsu EGASHIRA, Taiji IMOTO
Tetrahedron Lett. 33 3511 - 3514 1992年04月
掲載種別：研究論文（学術雑誌）
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Activated charcoal-mediated hydroxylation under very mild conditions: Conversion of physalin B into 25-hydroxyphysalin B 査読あり
Bunsho Makino, Masao Kawai, Tatsuo Yamamoto, Hatsuo Yamamura, Yasuo Butsugan, Mitsuo Hayashi, Kiyoshi Ogawa
Journal of the Chemical Society, Chemical Communications ( 19 ) 1430 - 1431 1992年
記述言語：英語 掲載種別：研究論文（学術雑誌）
Activated charcoal treatment of physalin B, a 13, 14-seco-16,24- cyclosteroidal constituent of Physalis alkekengi, in MeOH at room temperature yields a product possessing a hydroxy group at the α-position of the δ-lactone carbonyl function, namely 25-hydroxyphysalin B, in high yield.
DOI： 10.1039/C39920001430
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Physalins N and O from Physalis alkekengi 査読あり
Masao Kawai, Toichi Ogura, Bunsho Makino, Akihide Matsumoto, Hatsuo Yamamura, Yasuo Butsugan, Mitsuo Hayashi
Phytochemistry 31 ( 12 ) 4299 - 4302 1992年
記述言語：英語 掲載種別：研究論文（学術雑誌）
The structures of physalins N and O, isolated from Physalis alkekengi var. francheti, were determined as 7α-hydroxyphysalin B and (25S)-25,27-dihydrophysalin A, respectively. © 1992.
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Optical resolution of N-carbobenzoxy-α-methoxyglycine 査読あり
Masao Kawai, Yoshimasa Omori, Hatsuo Yamamura, Yasuo Butsugan
Tetrahedron: Asymmetry 3 ( 8 ) 1019 - 1020 1992年
記述言語：英語 掲載種別：研究論文（学術雑誌）
Optical resolution of racemic N-carbobenzoxy-α-methxyglycine using D/L-phenylalaninol or (1S,2S)-2-amino-1-phenyl-1,3-propanediol afforded (+)- and (-)-enantiomers, to which D-and L-configurations, respectively, were assigned based on the 1H NMR data and biological activity of demorphin N-terminal tetrapeptide analogs. © 1992.
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A Complete Set of beta-Cyclodextrin 6A, 6X-Diactivated by Two Different Sulfonyl Groups 査読あり
Kahee FUJITA, Hatsuo YAMAMURA, Taiji IMOTO
Tetrahedron Lett. 32 6737 - 6740 1991年04月
掲載種別：研究論文（学術雑誌）
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Preparation of Heptakis(6-O-(p-tosyl))- beta-cyclodextrin and Heptakis(6-O-(p-tosyl))-2-O-(p-tosyl)- beta-cyclodextrin and TheirConversion to Heptakis(3,6-anhydro)- beta-cyclodextrin 査読あり
Hatsuo YAMAMURA, Kahee FUJITA
Chem. Pharm. Bull. 39 2505 - 2508 1991年04月
掲載種別：研究論文（学術雑誌）
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Preparation of Heptakis(6-0-(/?-tosyl))-/j-cyclodextrin And Heptakis(6-o-(/>-tosyl))-2-0-(/?-tosyl)-/j-cyclodextrin And Their Conversion To Heptakis(3,6-anhydro)-/j-cyclodextrin 査読あり
Hatsuo Yamamura, Kahee Fujita'
Chemical and Pharmaceutical Bulletin 39 ( 10 ) 2505 - 2508 1991年
記述言語：英語 掲載種別：研究論文（学術雑誌）
Heptakis(6-0-(/>
-tosyl))-/?-cyclodextrin and heptakis(6-0-(/Mosyl))-2-O-(/>
-tosyl)-/J-cyclodextrin were prepared by the reaction of /?-cyclodextrin with p-tosyl chloride in pyridine. They were converted to heptakis(3,6-anhydro)-/?-cyclodextrin, constituted from alternative (1C4) glucose units. © 1991, The Pharmaceutical Society of Japan. All rights reserved.DOI： 10.1248/cpb.39.2505
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Specific Preparation and Structure Determination of 3A,3C,3E-Tri-O-sulfonyl- beta-cyclodextrin. 査読あり
Kahee FUJITA, Tsutomu TAHARA, Hatsuo YAMAMURA, Taiji IMOTO, Toshitaka KOGA, Toshihiro FUJIOKA, Kunihide MIHASHI
J. Org. Chem. 55 877 - 8808 1990年04月
掲載種別：研究論文（学術雑誌）
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Specific Preparation and Structure Determination of 3A,3C,3E-Tri-O-sulfonyl-β-cyclodextrin 査読あり
Kahee Fuiita1, Tsutomu Tahara, Toshitaka Koga, Hatsuo Yamamura, Taiii Imoto, Toshihiro Fujioka, Kunihide Mihashi
Journal of Organic Chemistry 55 ( 3 ) 877 - 880 1990年
記述言語：英語 掲載種別：研究論文（学術雑誌）
A reaction of β-cyclodextrin with β-naphthylsulfonyl chloride in alkaline aqueous acetonitrile gave only one isomer (3A,3c,3E-trisulfonate, 17.8%) of five 3,3,3-tri-O-sulfonyl-β-cyclodextrins. The isomer was converted to 3Af6A:3c,6c:3E,6E-trianhydro-β-cyclodextrin, the structure of which was assigned by comparing its spectral and HPLC data of the trianhydro-β-cyclodextrin with those of all authentic 3,6:3,6:3,6-trianhydro-β-cyclodextrins prepared by the reactions of known 6-tri-O-sulfonylated β-cyclodextrins with aqueous alkali. © 1990, American Chemical Society. All rights reserved.
DOI： 10.1021/jo00290a016
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6-O-TRISUBSTITUTED BETA-CYCLODEXTRINS WHOSE SUBSTITUENTS ARE DIFFERENT FROM ONE ANOTHER 査読あり
K FUJITA, A MATSUNAGA, H YAMAMURA, T IMOTO
CHEMISTRY LETTERS ( 12 ) 1947 - 1950 1988年12月
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Complete Sets of Structurally Determined 6A,6X-Unsymmetrically Disubstituted β-Cyclodextrins: 6A-S-Phenyl-6X-O-(β-Naphthylsulfonyl)-6A-Thio-β-Cyclodextrins and 6A-S-(tert-butyl)-6X-O-(β-Naphthylsulfonyl)-6A-thio-β-cyclodextrins 査読あり
Kahee Fujita, Atsuo Matsunaga, Hatsuo Yamamura, Taiji Imoto
Journal of Organic Chemistry 53 ( 19 ) 4520 - 4522 1988年09月
記述言語：英語 掲載種別：研究論文（学術雑誌）
Complete sets of structurally determined 6A,6X-unsymmetrically disubstituted β-cyclodextrins and 6A-S-phenyl-6X-O-(β-naphthylsulfonyl)-6A-thio-β-cyclodextrins and 6A-S-(tert-butyl)-6X-O-(β-naphthylsulfonyl)-6A-thio-β-cyclodextrins, were prepared, and their structures were determined. These constitute complete sets of cyclodextrins having two functional groups that are different from one another. © 1988, American Chemical Society. All rights reserved.
DOI： 10.1021/jo00254a019
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Synthesis of 6A,6X-Di-O-(p-tosyl)-gamma-cyclodextrins and Their Structural Determination through Enzymatic Hydrolysis of3A,6A;3X,6X-Dianhydro-gamma-cyclodextrins 査読あり
Kahee FUJITA, Hatsuo YAMAMURA, Taiji IMOTO, Toshiro FUJIOKA, Kunihide MIHASHI
J. Org. Chem. 53 1943 - 1947 1988年04月
掲載種別：研究論文（学術雑誌）
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Regiochemical Correlation between 6-O-Sulfonylated Cyclodextrins and 3-O-Sulfonylated Cyclodextrins via 3,6-Anhydrocyclodextrins. 査読あり
Kahee FUJITA, Tsutomu TAHARA, Yoshimitsu EGASHIRA, Hatsuo YAMAMURA, Taiji IMOTO, Toshitaka KOGA, Toshihiro FUJIOKA, Kunihide MIHASHI
Chem. Lett. ( 4 ) 705 - 708 1988年04月
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Preparation of 3A,6A-Anhydro-beta-cyclodextrin and Its Taka Amylolysis 査読あり
Kahee FUJITA, Hatsuo YAMAMURA, Taiji IMOTO, Iwao TABUSHI
Chem. Lett. ( 3 ) 543 - 546 1988年04月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：The Chemical Society of Japan
3<SUP>A</SUP>,6<SUP>A</SUP>-Anhydro-β-cyclodextrin was prepared by the reaction of 6-<I>O</I>-(<I>p</I>-tosyl)-β-cyclodextrin with aqueous alkali. This anhydrocyclodextrin was enzymatically hydrolyzed by Taka amylase to give 3″,6″-anhydromaltotetraose exclusively.
DOI： 10.1246/cl.1988.543
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Complete Sets of Structurally Determined 6A,6X-Unsymmetrically Disubstituted beta-Cyclodextrins:6A-S-Phenyl-6X-O-(b-naphthylsulfonyl)-6A-thio-beta-cyclodextrins and 6A-S-(tert-Butyl)-6X-O-(b-naphthylsulfonyl)-6A-thio-beta-cyclodextrins 査読あり
Kahee FUJITA, Atsuo MATSUNAGA, Hatsuo YAMAMURA, Taiji IMOTO
J. Org. Chem. 53 4520 - 4522 1988年04月
掲載種別：研究論文（学術雑誌）
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6-O-Trisubstituted beta-Cyclodextrins Whose Substituents Are Different from One Another 査読あり
Kahee FUJITA, Atsuo MATSUNAGA, Hatsuo YAMAMURA, Taiji IMOTO
Chem. Lett. 1947 - 1950 1988年04月
掲載種別：研究論文（学術雑誌）
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SYNTHESIS OF 6A,6X-DI-OMICRON-(PARA-TOSYL)-GAMMA-CYCLODEXTRINS AND THEIR STRUCTURAL DETERMINATION THROUGH ENZYMATIC-HYDROLYSIS OF 3A,6A-PARA3X,6X-DIANHYDRO-GAMMA-CYCLODEXTRINS 査読あり
K FUJITA, H YAMAMURA, T IMOTO, T FUJIOKA, K MIHASHI
JOURNAL OF ORGANIC CHEMISTRY 53 ( 9 ) 1943 - 1947 1988年04月
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Shigehiro KAMITORI, Ken HIROTSU, Taiichi HIGUCHI, Kahee FUJITA, Hatsuo YAMAMURA, Taiji IMOTO, Iwao TABUSHI
J. Chem. Soc. Perkin Trans. 1 7 - 14 1987年04月
掲載種別：研究論文（学術雑誌）
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6-Polysubstituted a-Cyclodextrins. Application of Korner's Absolute Method of Isomer Determination 査読あり
Kahee FUJITA, Hatsuo YAMAMURA, Atsuo YAMAMURA, Taiji IMOTO, Kunihide MIHASHI, Toshihiro FUJIOKA
J. Am. Chem. Soc. 108 4509 - 4513 1986年04月
掲載種別：研究論文（学術雑誌）
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Unsymmetrically Disubstituted beta-Cyclodextrins. 6A,6X-Dideoxy-6A-azido-6X [(mesitylsulfonyl)oxy] Derivatives. 査読あり
Kahee FUJITA, Hatsuo YAMAMURA, Taiji IMOTO
J. Org. Chem. 50 4393 - 4395 1985年04月
掲載種別：研究論文（学術雑誌）
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UNSYMMETRICALLY DISUBSTITUTED BETA-CYCLODEXTRINS - 6A,6X-DIDEOXY-6A-AZIDO-6X-[(MESITYLSULFONYL)OXY] DERIVATIVES 査読あり
K FUJITA, H YAMAMURA, T IMOTO
JOURNAL OF ORGANIC CHEMISTRY 50 ( 22 ) 4393 - 4395 1985年
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