11 カスガマイシンの構造

概要

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Kasugamycin is an antibiotic produced by Streptomyces kasugaensis and exhibits inhibition against various kinds of bacteria. including Pseudomonas and a strong preventive effect against rice blast. The chemical degradation of kasugamycin afforded three main fragments, i.e., d-inositol, methylkasugaminide (II), and kasuganobiosamine (I). The structure of methyl kasugaminide (II) was studied by mainly spectroscopic methods and determined to be methyl 2,3,4,6-tetradeoxy-2,4-diaminohexopyranoside, and it should be mentioned that to the best of our knowledge this is the first isolation from natural products. After structural determination of kasuganobiosamine (I) and kasugamycinic acid (IV), and preparation of each two isomers (V〜VIII) of monoacetyl- and monooxamide-derivatives of kasuganobiosamine (I), kasuganobiosamine (I) was chemically transformed to kasugamycin having an unique amidine structure which attached to 4-amino group of the sugar moiety. The gross structure of kasugamyoin (K) is proposed, since the linking position of d-inositol with kasugamine has been determined by X-ray crystallographic analysis.
天然有機化合物討論会の論文
1966-09-15