29 抗生物貭Althiomycinの構造決定

概要

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Althiomycin (I, C_<16>H_<17>O_6N_5S_2) is an interesting antibiotic isolated from the culture filtrate of Streptomyces althioticus in 1957 and inhibits growth of both Gram-positive and -negative bacteria. The structural study of althiomycin was carried out in the following way. The hydrolysis of I with 6N-HCl afforded DL-cysteic acid (II), DL-serine (III), glycine, thiazole-4-carboxylic acid (IV) and ammonia. The hydrolysis with 2N-NaOH afforded 2-(hydroxyinimomethyl)-thiazole-4-carboxylic acid (V) as a key degradation product. The simple methanolysis gave 4-methoxy-3-pyrroline-2-one (VIII) and a methyl ester composed of C_<12>H_<12>O_4N_4S_2. Based on the chemical degradations and spectroscopic evidence of each compound, Ia or Ib was considered to be most reasonable structure for althiomycin. On the other hand, X-ray crystal analysis of didehydroalthiomycin (XV) unambig-uously demonstrated that the structure of I contains the thiazoline system of Ia rather than eight-membered ring system of Ib. Thus, the structure of althiomycin has been shown to be N-[2-hydroxy-1-[4-[(4-methoxy-2-oxo-3-pyrrolin-1-yl)carbonyl]-2-thiazoline-2-yl]ethyl]2-(hydroxyiminomethyl)-4-thiazolicarboxamide.
天然有機化合物討論会の論文
1973-10-01