TY - JOUR
T1 - IspG converts an epoxide substrate analogue to (E)-4-hydroxy-3-methylbut-2- enyl diphosphate
T2 - Implications for IspG catalysis in isoprenoid biosynthesis
AU - Nyland, Rodney L.
AU - Xiao, Youli
AU - Liu, Pinghua
AU - Freel Meyers, Caren L.
PY - 2009/12/16
Y1 - 2009/12/16
N2 - (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.
AB - (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.
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U2 - 10.1021/ja907470n
DO - 10.1021/ja907470n
M3 - Article
C2 - 19919056
AN - SCOPUS:71749113661
SN - 0002-7863
VL - 131
SP - 17734
EP - 17735
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 49
ER -