Studies of unusual amino acids and their peptides. VI. The synthese and the optical resolutions of .BETA.-methylphenylalanine and its dipeptide present in bottromycin.

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概要

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• β-Methyl-phenylalanine was prepared by the condensation of α-methylbenzyl bromide with acetaminomalonate, followed by the hydrolysis and decarboxylation of the condensate. The decarboxylation occurred diastereoselectively to some extent. The <I>erythro</I> and the <I>threo</I> isomers could be separated by the fractional crystallization of their benzoyl derivatives, and differentiated by means of their NMR spectra. The optical resolution of the respective isomers was attained by treating the benzyloxycarbonyl derivatives with qunine or quinidine; thus, the four isomers could be obtained in a pure state. A dipeptide present in the C-terminal of bottromycin was synthesized by coupling N-protected <I>erythro</I>-L-β-methyl-phenylalanine with either L-β-(2-thiazolyl)-β-alanine ester or, more conveniently, with the DL-compound, and by separating thereafter.

• 公益社団法人 日本化学会の論文

著者

• Watanabe Hiroshi

  Laboratory Of Toxicology Central Research Laboratories Of Meiji Seika Kaisha Ltd.

• Yamada Takashi

  Laboratory Of Nutritional Biochemistry Graduate School Of Nutritional And Environmental Sciences University Of Shizuoka

• Kuwata Shigeru

  Laboratory of Chemistry Faculty of Science K\={o}nan University

• Kataoka Yoshiharu

  Laboratory of Chemistry, Faculty of Science, K\={o}nan University

• Seto Yasuhiko

  Laboratory of Chemistry, Faculty of Science, K\={o}nan University

• Yamamoto Masaaki

  Laboratory of Chemistry, Faculty of Science, K\={o}nan University

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• Studies of unusual amino acids and their peptides. VI. The synthese and the optical resolutions of .BETA.-methylphenylalanine and its dipeptide present in bottromycin.
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