Synthesis of four stereoisomers of .GAMMA.-hydroxyarginine via the corresponding isomers of .GAMMA.-hydroxyornithine.
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概要
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Diastereomeric γ-hydroxy-L- and D-ornithines were prepared by reduction of the corresponding γ-oxoornithines synthesized from L- and D-histidines with sodium borohydride. The isomeric composition of the product obtained from L-histidine was estimated to be 68% <I>erythro</I> and 32% <I>threo</I> isomers and that of the product from D-histidine 65% <I>erythro</I> and 35% <I>threo</I> isomers by automatic amino acid analysis after conversion of the basic amino acids into neutral <I>N</I><SUP>δ</SUP>-acetyl derivatives. The diastereoisomers of each γ-hydroxyorni thine were separated by chromatography on a Dowex 50 column, four optically active isomers being isolated as their hydrochlorides in crystalline state. Guanidination of these isomers with 1-amidino-3,5-dimethylpyrazole nitrate (ADPN) gave the corresponding optically active isomers of γ-hydroxyarginine which were isolated as crystalline hydrochlorides. <I>Erythro</I>-γ-hydroxy-L-arginine hydrochloride shows a specific rotation which agrees very closely with that of natural product of γ-hydroxyarginine.
- 公益社団法人 日本化学会の論文
著者
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Makisumi Satoru
Department Of Chemistry Faculty Of Science Kyushu University
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Makisumi Satoru
Department of Chemistry, Faculty of Science, Kyushu University 33
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Mizusaki Koichi
Department of Chemistry, Faculty of Science, Kyushu University
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- Synthesis of four stereoisomers of .GAMMA.-hydroxyarginine via the corresponding isomers of .GAMMA.-hydroxyornithine.