Enantioconvergent hydrolysis of styrene epoxides by newly discovered epoxide hydrolases in mung bean.
[reaction: see text] Two novel epoxide hydrolases were discovered in mung bean (Phaseolus radiatus L.) for the first time, either of which can catalyze enantioconvergent hydrolysis of styrene epoxides. Their regioselectivity coefficients are more than 90% for the p-nitrostyrene oxide. Furthermore, the crude mung bean powder was also shown to be a cheap and practical biocatalyst, allowing a one-step asymmetric synthesis of chiral (R)-diols from racemic epoxides, in up to >99% ee and 68.7% overall yield (after recrystallization).
Xu
Wei
W
Laboratory of Biocatalysis and Bioprocessing, State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China.
Xu
Jian-He
JH
Pan
Jiang
J
Gu
Qing
Q
Wu
Xin-Yan
XY
D002384:Catalysis; D004851:Epoxide Hydrolases / Q000737:chemistry / Q000302:isolation & purification*; D004852:Epoxy Compounds / Q000737:chemistry*; D007887:Fabaceae / Q000737:chemistry*; D006868:Hydrolysis; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D020058:Styrene / Q000737:chemistry*
D004852:Epoxy Compounds; D020058:Styrene; D004851:Epoxide Hydrolases