Synthesis of four diastereoisomers of histopine.

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概要

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• Four isomers of histopine, <I>N</I><SUP>2</SUP>-(1-carboxyethyl)histidine, were prepared to provide their physicochemical properties. A diastereomeric mixture, (<I>RS</I>),(<I>S</I>)-histopine (<I>N</I><SUP>2</SUP>-[(<I>RS</I>)-1-carboxyethyl]-(<I>S</I>)-histidine), was synthesized from 2-oxopropionic acid and (<I>S</I>)-histidine by reduction with sodium cyanoborohydride. The mixture was separated into its components, (<I>S</I>),(<I>S</I>)-histopine and (<I>R</I>),(<I>S</I>)-histopine, by an ion-exchange column chromatography. In a similar manner (<I>R</I>),(<I>R</I>)-histopine and (<I>S</I>),(<I>R</I>)-histopine were prepared. Configurations of the four isomers obtained were assumed from their ORD data by comparison with those of the isomers of octopine (<I>N</I><SUP>2</SUP>-(1-carboxyethyl)arginine) with a definite configuration.

• 公益社団法人 日本化学会の論文

著者

• Waki Michinori

  Laboratory Of Biochemistry Department Of Chemistry Faculty Of Science Kyushu University

• Izumiya Nobuo

  Laboratory Of Biochemistry Faculty Of Engineering Kyushu Sangyo University

• Izumiya Nobuo

  Laboratory of Biochemistry, Faculty of Science, Kyushu University 33

• Kitajima Yasuo

  Laboratory of Biochemistry, Faculty of Science, Kyushu University 33

• Waki Michinori

  Laboratory of Biochemistry, Faculty of Science, Kyushu University 33

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