STRUCTURAL ELUCIDATION AND SOLUTION CONFORMATION OF THE NOVEL HERBICIDE HYDANTOCIDIN

被引:118
作者
HARUYAMA, H
TAKAYAMA, T
KINOSHITA, T
KONDO, M
NAKAJIMA, M
HANEISHI, T
机构
[1] SANKYO CO LTD,DEPT TECH LICENSING,CHUO KU,TOKYO 140,JAPAN
[2] SANKYO CO LTD,FERMENTAT RES LAB,SHINAGAWA KU,TOKYO 140,JAPAN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 07期
关键词
D O I
10.1039/p19910001637
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The structure of a novel herbicide, hydantocidin isolated from the fermentation broth of Streptomyces hygroscopics SANK 63584, was determined by the combined analysis of MS and H-1 NMR spectra. Hydantocidin is a novel spiro compound containing a subofuranoid ring, at the anomeric position of which a hydantoin ring is used such that the C(1)-N(1) linkage is beta. The relative configuration and the conformation in solution was determined by quantitative analysis of the NOE spectra and T1 values. In CD3OD and [H-2(6)]DMSO (dimethyl sulphoxide) solutions, the ribofuranose moiety of hydantocidin was found to be fixed in a C2-endo conformation, probably due to the rigidity of the spiro structure and hydrogen bonding between 3-OH and the carbonyl group at C-4'.
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页码:1637 / 1640
页数:4
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