Abstract
Mechanistic differences between type I and type II dehydroquinases have been exploited in the design of type specific inhibitors. (2R)-2-Bromo-3-dehydroquinic acid (3), (2R)-2-fluoro-3-dehydroquinic acid (5) and 2-bromo-3-dehydroshikimic acid (4), all excellent substrates for type II dehydroquinase, are shown to be irreversible inhibitors of type I dehydroquinase.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Enzyme Inhibitors / pharmacology*
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Escherichia coli / enzymology
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Hydro-Lyases / antagonists & inhibitors*
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Hydro-Lyases / metabolism*
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Mycobacterium tuberculosis / enzymology
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Quinic Acid / analogs & derivatives*
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Quinic Acid / chemical synthesis
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Quinic Acid / pharmacology
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Shikimic Acid / analogs & derivatives*
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Shikimic Acid / chemical synthesis
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Shikimic Acid / metabolism
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Shikimic Acid / pharmacology
Substances
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2-bromo-3-dehydroquinic acid
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2-bromo-3-dehydroshikimic acid
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2-fluoro-3-dehydroquinic acid
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Enzyme Inhibitors
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Quinic Acid
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Shikimic Acid
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Hydro-Lyases
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3-dehydroquinate dehydratase