Papers - YAMAMURA Hatsuo

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  • Stereodivergent Allylindation of Cyclopropenes. Remarkable Stereodirection and Aaceleration by Neighbouring Carboxyl and HydroxylGroups Reviewed

    Shuki ARAKI, Hiroyuki NAKANO, Kandasamy SUBBURAJ, Syunehisa HIRASHITA, Kensuke SHIBUTANI, Hastuo YAMAMURA, Masao KAWAI, YasuoBUTSUGAN

    Tetrahedron Lett   39   6327 - 6330   1998.04

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  • Stereochemistry of Protected Ornithine Side Chains in Gramicidin D Derivatives and Their Resistance to N-Methylation Reviewed

    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   1998.04

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  • Primary Hydrocy-modified Cyclomaltoheptaose Derivatives with Two Kinds of Substituents. Preparation of 6I-(Benzyloxycarbonylamino)-,6I-(tert-Butoxycarbonylamino)- and 6I-Azido-6I-deoxy-6II,6III,6IV, 6V, 6VI, 6VII, hexa-O-tosylcyclomaltoheptaose and Their Conversion to theHexakis(3,6-anhydro) derivative Reviewed

    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   1998.04

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  • Preparation and Metal Ion-binding of Gramicidin S Derivatives Carrying Picolinoyl Groups on the Ornithine Side Chains Reviewed

    Keiichi YAMADA, Hirotaka OZAKI, Naoki KANDAa, Hastuo YAMAMURA, Shuki Araki, Masao KAWAI

    J. Chem. Soc., Perkin Trans. 1   3999 - 4004   1998.04

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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 Reviewed

    Shuki ARAKI, Kaori YAMAMOTO, Misako YAGI, Tomoko INOUE, Hiroyo FUKUNAGA, Hiromi HATTORI, Hastuo YAMAMURA, Masao KAWAI, YasuoBUTSUGAN

    Eur. J. Org. Chem.   121 - 127   1998.04

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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 Reviewed

    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   1998.04

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher: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 Reviewed

    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

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher: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 Reviewed

    Masafumi YAMADA, Koji TANAKA, Yasuo BUTSUGAN, Masao KAWAI, Hastuo YAMAMURA, Shuki ARAKI

    Main Group Metal Chemistry   20 ( 4 )   241 - 246   1997.04

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:FREUND PUBLISHING HOUSE  

    New indium hydride reagents LiPhnInHe4-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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  • High gamma-Selectivity in the Coupling of Penta-2,4-dienyl- and Pent-2-en-4-ynylindium Reagents with Aldehy Reviewed

    Tsunehisa HIRASHITA, Shi'ichiro INOUE, Hastuo YAMAMURA, Masao KAWAI, Shuki ARAKI

    J. Organometalic Chemistry   549   305 - 309   1997.04

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  • Diastereoselective Reduction of Acyclic Hydroxyketones and Diketones with an Indium Hydride Reagent Reviewed

    Masafumi YAMADA, Tomoaki Horie, Masao KAWAI, Hastuo YAMAMURA, Shuki ARAKI

    Tetrahedron   53   15685 - 15690   1997.04

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  • Convenient Enantioselective Preparation of Salsolinol-1-carboxylic Acid Reviewed

    Masao KAWAI, Yulin Deng, Ikuko KIMURA, Hatsuo YAMAMURA, Shuki ARAKI, Makoto NAOI

    Tetrahedron: Asymmetry   8   1487 - 1490   1997.04

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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 Reviewed

    Yulin Deng, Wakako MARUYAMA, Masao KAWAI, Philippe Dostert, Hatsuo YAMAMURA, Tsutomu TAKAHASHI, Makoto NAOI

    J. Chromatography B.   689   313 - 320   1997.04

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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 Reviewed

    J. Chromatography B.   689   313 - 320   1997.04

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  • Selective reduction of organic functional groups with indium hydride reagents Reviewed

    Masafumi Yamada, Koji Tanaka, Yasuo Butsugan, Masao Kawai, Hatsuo Yamamura, Shuki Araki

    Main Group Metal Chemistry   20 ( 4 )   241 - 246   1997

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher: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.

    DOI: 10.1515/MGMC.1997.20.4.241

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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 Reviewed

    YL Deng, W Maruyama, H Yamamura, M Kawai, P Dostert, M Naoi

    ANALYTICAL CHEMISTRY   68 ( 17 )   2826 - 2831   1996.09

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher: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 Reviewed

    Bunsho MAKINO, Masao KAWAI, Toichi OGURA, Masaki NAKANISHI, Hatsuo YAMAMURA, Yasuo BUSTUGAN

    J. Natural Products   58   1668 - 74   1996.04

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  • Preparation of Protected alpha-Alkoxyglycines. Reviewed

    Masao KAWAI, Kouji HOSODA, Yoshimasa Omori, Keiichi YAMADA, Shiko HAYAKAWA, Hatsuo YAMAMURA, Yasuo BUSTUGAN

    Synthetic Communications   26   1545 - 1554   1996.04

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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. Reviewed

    Yulin Deng, Wakako MARUYAMA, Hatsuo YAMAMURA, Masao KAWAI, Philippe Dostert, Makoto NAOI

    Anal. Chem.   68   2826 - 2831   1996.04

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  • Indium-mediated Reaction of 1,3-Dichloro- and 1,3-Dibromopropens with Carbonyl Compounds. Generation of Novel 3,3-Diindiopropene. Reviewed

    Shuki ARAKI, Tsunehisa HIRASHITA, Hidetaka SHIMIZU, Hatsuo YAMAMURA, Masao KAWAI, Yasuo BUTSUGAN

    Tetrahedron Lett.   37   8417 - 8420   1996.04

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  • Dependence of Guest-binding Ability on Cavity Shape of Deformed Cyclodextrins. Reviewed

    Kahee FUJITA, Yuji OKABE, Kazuko OHTA, Hatsuo YAMAMURA, Tsutomu TAHARA, Yasuyoshi NOGAMI, Toshitaka KOGA

    Tetrahedron Lett.   37   1825 - 1828   1996.04

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