Configuration of alanine part in natural octopine.
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概要
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Octopine has a structure of <I>N</I><SUP>2</SUP>-(1-carboxyethyl)arginine or <I>N</I>-(1-carboxy-4-guanidinobutyl)alanine. Configuration of the arginine part in natural octopine is determined as (<I>S</I>), whereas that of the alanine part has been assumed as (<I>R</I>). The configuration of the alanine part was concluded to be (<I>R</I>) by the present synthesis of (+)-octopine, which was identical with the natural one, by a sequence of reactions starting from (<I>R</I>)-alanine and (<I>R</I>)-2-bromo-5-acetamidopentanoic acid. The reaction of (<I>R</I>)-alanine and (<I>R</I>)-2-bromo-5-acetamidopentanoic acid in alkaline conditions gave <I>N</I><SUP>2</SUP>-((<I>R</I>)-1-carboxyethyl)-<I>N</I><SUP>5</SUP>-acetyl-(<I>S</I>)-ornithine which was converted to <I>N</I><SUP>2</SUP>-((<I>R</I>)-1-carboxyethyl)-(<I>S</I>)-ornithine ((<I>R</I>),(<I>S</I>)-octopinic acid) by hydrolysis with hydrochloric acid. (<I>R</I>),(<I>S</I>)-Octopinic acid gave (+)-octopine ((<I>R</I>),(<I>S</I>)-octopine) by guanidination. The reaction of (<I>S</I>)-alanine and (<I>R</I>)-2-bromo-5-acetamidopentanoic acid led to give (<I>S</I>),(<I>S</I>)-octopinic acid and subsequently (+)-isooctopine ((<I>S</I>),(<I>S</I>)-octopine).
- 公益社団法人 日本化学会の論文
著者
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Waki Michinori
Laboratory Of Biochemistry Department Of Chemistry Faculty Of Science Kyushu University
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Izumiya Nobuo
Laboratory Of Biochemistry Faculty Of Engineering Kyushu Sangyo University
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Kitajima Yasuo
Laboratory of Biochemistry, Faculty of Science, Kyushu University 33
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Mitsuyasu Nobuo
Laboratory of Biochemistry, Faculty of Science Kyushu University 33,
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Goto Kazuo
Laboratory of Biochemistry, Faculty of Science, Kyushu University 33
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