(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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Bibliographische Detailangaben
Veröffentlicht in:	Organic & biomolecular chemistry 2004-06, Vol.2 (11), p.1592-1596
Hauptverfasser:	Frederickson, Martyn, Roszak, Aleksander W, Coggins, John R, Lapthorn, Adrian J, Abell, Chris
Format:	Artikel
Sprache:	eng
Schlagworte:	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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Beschreibung
Zusammenfassung:	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