BIOSYNTHESIS OF BERNINAMYCIN - INCORPORATION OF C-13-LABELED AMINO-ACIDS

被引：21

作者：

LAU, RCM ^{[1
]}

RINEHART, KL ^{[1
]}

机构：

[1] UNIV ILLINOIS, ROGER ADAMS LAB, URBANA, IL 61801 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1995年 / 117卷 / 29期

关键词：

D O I：

10.1021/ja00134a004

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two-dimensional NMR and FABMS/MS studies agree with the structure for berninamycin A proposed by Abe et al. (Tetrahedron Lett. 1988, 29, 1401-1404). Biosynthetic studies with C-13-enriched amino acids confirm our earlier results that the dehydroalanine units are formed by dehydration of serine. The oxazoles are formed by condensing a threonine unit with a serine or another threonine with dehydration, and the thiazole is formed by combining a cysteine with a serine with dehydration. The biosynthesis of the pyridine ring is similar to piperidine/hydroxypyridine ring formation in thiostrepton and nosiheptide. The biogenesis of berninamycin A is also discussed.

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页码：7606 / 7610

页数：5

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