Abstract
IspG is an intriguing enzyme in bacteria, parasite, and plant isoprenoid biosynthesis, and its catalytic mechanism remains elusive. We report here the synthesis of (2R,3R)-4-hydroxy-3-methyl-2,3-epoxybutanyl diphosphate (Epoxy-HMBPP), a proposed intermediate in one of the frequently cited mechanistic models. We have also demonstrated that this epoxide analogue is a catalytically competent IspG substrate. This study represents the first mechanistic study of this important enzyme.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Alkyl and Aryl Transferases / metabolism*
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Biocatalysis
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Epoxy Compounds / chemistry
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Epoxy Compounds / metabolism*
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Organophosphorus Compounds / chemistry
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Organophosphorus Compounds / metabolism*
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Terpenes / chemistry
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Terpenes / metabolism*
Substances
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(E)-4-hydroxy-3-methylbut-2-enyl diphosphate
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Epoxy Compounds
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Organophosphorus Compounds
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Terpenes
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Alkyl and Aryl Transferases