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新型螺环缩酮类大环内酯A82548A的结构

Structure of the new spiroketal-macrolide A82548A.

作者信息

Kirst H A, Larsen S H, Paschal J W, Occolowitz J L, Creemer L C, Steiner J L, Lobkovsky E, Clardy J

机构信息

Lilly Research Laboratories, Greenfield, Indiana 46140, USA.

出版信息

J Antibiot (Tokyo). 1995 Sep;48(9):990-6. doi: 10.7164/antibiotics.48.990.

DOI:10.7164/antibiotics.48.990
PMID:7592067
Abstract

A new member of the spiroketal-containing macrolide class of fermentation-derived natural products was isolated from mycelial extracts of Streptomyces diastatochromogenes. The principal component, A82548A, was shown to possess a 22-membered macrolide ring system onto which was incorporated both a spiroketal and a hemiketal moiety. Relative stereochemistry was established by single crystal X-ray diffraction studies. Absolute stereochemistry was determined via hydrolysis of the amino sugar glycosidically linked to the aglycone, which was identified as L-kedarosamine. The overall three-dimensional structure is closely related to that of the macrolides cytovaricin, rutamycin, and ossamycin.

摘要

从龟裂链霉菌的菌丝体提取物中分离出一种新型含螺环缩酮结构的发酵衍生天然产物大环内酯类化合物。主要成分A82548A具有一个22元大环内酯环系统,其上同时并入了一个螺环缩酮和一个半缩酮部分。通过单晶X射线衍射研究确定了相对立体化学结构。通过对糖苷键连接到苷元上的氨基糖进行水解确定了绝对立体化学结构,该氨基糖被鉴定为L-来苏糖胺。其整体三维结构与大环内酯类化合物细胞霉素、鲁塔霉素和骨霉素密切相关。

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