Component Amino Acids of the Antibiotic Longicatenamycin. Isolation of 5-Chloro-D-tryptophan

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概要

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• An amino acid composition of the pep tide antibiotic longicatenamycin was investigated. Four new amino acids, <I>i.e.</I>, <I>thero</I>-β-hydroxy-L-glutamic acid, L-2-amino-5-rnethylhexanoic acid, L-2-amino-6-methylheptanoic acid, and L-2-amino-7-methyloctanoic acid, which were reported by Shoji <I>et al.</I>, were reconfirmed by comparison with the synthetic specimens. Racemic forms of the latter three amino acids were synthesized through acetaminomalonate method. Furthermore, 5-chloro-D-tryptophan was newly isolated from the hydrolyzate of the antibiotic. This structure was assigned by NMR, MS and ORD. A steric configuration of this amino acid was certified by degradation to D-aspartic acid through ozonization. 5-Chloro-DL-tryptophan was synthesized from 3-cyanopropionaldehyde and <I>p</I>-chlorophenylhydrazine by Fischer's indole synthesis.

• 公益社団法人 日本化学会の論文

著者

• Shiba Tetsuo

  Department Of Chemistry Faculty Of Science Osaka University

• Akiyama Hitoshi

  Department Of Drug Metabolism Tokushima Research Institute Otsuka Pharmaceutical Co. Ltd.

• Mukunoki Yasuo

  Department of Chemistry, Faculty of Science, Osaka University

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