(1R,4S,5R)-3-Fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid: the fluoro analogue of the enolate intermediate in the reaction catalyzed by type II dehydroquinases

The fluoro analogue of the enolate intermediate in the reaction catalyzed by type II dehydroquinases has been prepared from naturally occurring (-)-quinic acid over seven steps and has been shown to be the most potent inhibitor reported to date of the type II enzyme from Mycobacterium tuberculosis.

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2004-06, Vol.2 (11), p.1592-1596
Main Authors: Frederickson, Martyn, Roszak, Aleksander W, Coggins, John R, Lapthorn, Adrian J, Abell, Chris
Format: Article
Language:English
Subjects:
Catalysis
Crystallography, X-Ray
Cyclohexanecarboxylic Acids - chemical synthesis
Cyclohexanecarboxylic Acids - chemistry
Cyclohexanecarboxylic Acids - pharmacology
Cyclohexenes
Enzyme Inhibitors - chemical synthesis
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - pharmacology
Hydro-Lyases - chemistry
Models, Molecular
Molecular Structure
Mycobacterium tuberculosis - enzymology
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Description
Summary:The fluoro analogue of the enolate intermediate in the reaction catalyzed by type II dehydroquinases has been prepared from naturally occurring (-)-quinic acid over seven steps and has been shown to be the most potent inhibitor reported to date of the type II enzyme from Mycobacterium tuberculosis.
ISSN:1477-0520
1477-0539
DOI:10.1039/b404535a