Abstract
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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Catalysis
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Crystallography, X-Ray
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Cyclohexanecarboxylic Acids / chemical synthesis
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Cyclohexanecarboxylic Acids / chemistry*
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Cyclohexanecarboxylic Acids / pharmacology
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Cyclohexenes
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Enzyme Inhibitors / chemical synthesis
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Enzyme Inhibitors / chemistry*
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Enzyme Inhibitors / pharmacology
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Hydro-Lyases / chemistry*
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Models, Molecular
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Molecular Structure
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Mycobacterium tuberculosis / enzymology
Substances
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3-fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid
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Cyclohexanecarboxylic Acids
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Cyclohexenes
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Enzyme Inhibitors
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Hydro-Lyases
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3-dehydroquinate dehydratase