当前位置： SCI文献检索 > JOURNAL OF MEDICINAL CHEMISTRY期刊下所有文献 > Structure-activity relationships at the 5-position of thiolactomycin: an intact (5R)-isoprene unit is required for activity against the condensing enzymes from Mycobacterium tuberculosis and Escherichia coli.

Structure-activity relationships at the 5-position of thiolactomycin: an intact (5R)-isoprene unit is required for activity against the condensing enzymes from Mycobacterium tuberculosis and Escherichia coli.

Abstract：

:Thiolactomycin inhibits bacterial cell growth through inhibition of the beta-ketoacyl-ACP synthase activity of type II fatty acid synthases. The effect of modifications of the 5-position isoprenoid side chain on both IC(50) and MIC were determined. Synthesis and screening of a structurally diverse set of 5-position analogues revealed very little tolerance for substitution in purified enzyme assays, but a few analogues retained MIC, presumably through another target. Even subtle modifications such as reducing one or both double bonds of the diene were not tolerated. The only permissible structural modifications were removal of the isoprene methyl group or addition of a methyl group to the terminus. Cocrystallization of these two inhibitors with the condensing enzyme from Escherichia coli revealed that they retained the TLM binding mode at the active site with reduced affinity. These results suggest a strict requirement for a conjugated, planar side chain inserting within the condensing enzyme active site.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Kim P,Zhang YM,Shenoy G,Nguyen QA,Boshoff HI,Manjunatha UH,Goodwin MB,Lonsdale J,Price AC,Miller DJ,Duncan K,White SW,Rock CO,Barry CE 3rd,Dowd CS

doi

10.1021/jm050825p

keywords:

subject

Has Abstract

pub_date

2006-01-12 00:00:00

pages

159-71

issue

1

eissn

0022-2623

issn

1520-4804

journal_volume

49

pub_type

杂志文章

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