Biosynthesis of cylindrospermopsin

被引：55

作者：

Burgoyne, DL

Hemscheidt, TK

Moore, RE ^{[1
]}

Runnegar, MTC

机构：

[1] Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA

[2] Univ So Calif, Med Ctr, Dept Med, Los Angeles, CA 90033 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 01期

关键词：

D O I：

10.1021/jo991257m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Studies on the biosynthesis of cylindrospermopsin (1), a potent hepatotoxin associated with the cyanobacterium Cylindrospermopsis raciborskii, indicate that 1 is an acetogenin with guanidinoacetic acid serving as the starter unit of the polyketide chain. Feeding experiments show that C14 and C15 of 1 are derived from C1 and C2 of glycine, respectively, and C4 through C13 arise from five contiguous acetate units attached head to tail. The methyl carbon on C13 originates from the C-1 pool. The starter unit, established by the incorporation of [guanidino-C-13,alpha-N-15]-guanidi-noacetic acid into N16 and C17 of 1, does not appear to be formed from glycine by known amidination pathways. The origin of the NH-CO-NH segment in the uracil ring is also unknown.

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页码：152 / 156

页数：5

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