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巴尔姆霉素的分离、结构鉴定和全合成。

Isolation, structural assignment, and total synthesis of barmumycin.

机构信息

Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona, Baldiri Reixac 10, E-08028 Barcelona, Spain.

出版信息

J Org Chem. 2010 Dec 17;75(24):8508-15. doi: 10.1021/jo101834c. Epub 2010 Nov 23.

DOI:10.1021/jo101834c
PMID:21090754
Abstract

Barmumycin was isolated from an extract of the marine actinomycete Streptomyces sp. BOSC-022A and found to be cytotoxic against various human tumor cell lines. On the basis of preliminary one- and two-dimensional (1)H and (13)C NMR spectra, the natural compound was initially assigned the structure of macrolactone-type compound 1, which was later prepared by two different routes. However, major spectroscopic differences between isolated barmumycin and 1 led to revision of the proposed structure as E-16. On the basis of the synthesis of this new compound, and subsequent spectroscopic comparison of it to an authentic sample of barmumycin, the structure of the natural compound was indeed confirmed as that of E-16.

摘要

巴尔姆霉素从海洋放线菌链霉菌属 BOSC-022A 的提取物中分离得到,对多种人肿瘤细胞系具有细胞毒性。根据初步的一维和二维(1)H 和(13)C NMR 谱,天然化合物最初被分配大环内酯型化合物 1 的结构,后来通过两种不同的路线制备。然而,分离出的巴尔姆霉素和 1 之间的主要光谱差异导致对所提出的结构进行了修订,作为 E-16。基于该新化合物的合成,并随后对其与巴尔姆霉素的真实样品进行光谱比较,确认了天然化合物的结构确实为 E-16。

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