Issue 7, 1991

Structural elucidation and solution conformation of the novel herbicide hydantocidin

Abstract

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 1H 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 β. The relative configuration and the conformation in solution was determined by quantitative analysis of the NOE spectra and T1 values. In CD3OD and [2H6]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′.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1991, 1637-1640

Structural elucidation and solution conformation of the novel herbicide hydantocidin

H. Haruyama, T. Takayama, T. Kinoshita, M. Kondo, M. Nakajima and T. Haneishi, J. Chem. Soc., Perkin Trans. 1, 1991, 1637 DOI: 10.1039/P19910001637

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