期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 353, 期 9, 页码 1510-1518出版社
WILEY-BLACKWELL
DOI: 10.1002/adsc.201100031
关键词
enantioselectivity; epoxide hydrolase; glycidyl ethers; kinetic resolution; molecular modeling
资金
- National Natural Science Foundation of China [20902023, 31071604]
- Ministry of Science and Technology, PR. China [2011CB710800, 2009ZX09501-016]
- China National Special Fund for State Key Laboratory of Bioreactor Engineering [2060204]
A novel epoxide hydrolase (BMEH) with unusual (R)-enantioselectivity and very high activity was cloned from Bacillus megaterium ECU1001. Highest enantioselectivities (E > 200) were achieved in the bioresolution of ortho-substituted phenyl glycidyl ethers and para-nitrostyrene oxide. Worthy of note is that the substrate structure remarkably affected the enantioselectivities of the enzyme, as a reversed (S)-enantiopreference was unexpectedly observed for the ortho-nitrophenyl glycidyl ether. As a proof-of-concept, five enantiopure epoxides (> 99% ee) were obtained in high yields, and a gram-scale preparation of (S)-ortho-methylphenyl glycidyl ether was then successfully performed within a few hours, indicating that BMEH is an attractive biocatalyst for the efficient preparation of optically active epoxides.
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