IspG converts an epoxide substrate analogue to (E)-4-hydroxy-3-methylbut-2- enyl diphosphate: Implications for IspG catalysis in isoprenoid biosynthesis

Rodney L. Nyland, Youli Xiao, Pinghua Liu, Caren L Meyers

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish (US)
Pages (from-to)17734-17735
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number49
DOIs
StatePublished - Dec 16 2009

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Epoxy Compounds
Biosynthesis
Terpenes
Catalysis
Enzymes
Diphosphates
Substrates
Bacteria
Parasites
(E)-4-hydroxy-3-methylbut-2-enyl diphosphate

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

IspG converts an epoxide substrate analogue to (E)-4-hydroxy-3-methylbut-2- enyl diphosphate : Implications for IspG catalysis in isoprenoid biosynthesis. / Nyland, Rodney L.; Xiao, Youli; Liu, Pinghua; Meyers, Caren L.

In: Journal of the American Chemical Society, Vol. 131, No. 49, 16.12.2009, p. 17734-17735.

Research output: Contribution to journalArticle

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