title: Synthesis of enantiopure glycidol derivatives via a one-pot two-step enzymatic cascade.
abstract: Styrene monooxygenase (SMO) can catalyze the kinetic resolution of secondary allylic alcohols to provide enantiopure glycidol derivatives. To overcome the low theoretical yield of kinetic resolution, we designed a one-pot two-step enzymatic cascade using prochiral α,β-unsaturated ketones as the substrates. An S-specific ketoreductase ChKRED03 was screened for the efficient bioreduction of the substrates to provide (S)-allylic alcohols, which underwent SMO-catalyzed epoxidation to achieve glycidol derivatives with contiguous stereogenic centers. Excellent enantioselectivity (ee > 99%) and diastereoselectivity (de > 99%) were achieved for the majority of the substrates, and product yields reached up to >99%.
authors.affiliation: Key Laboratory of Environmental and Applied Microbiology, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China. wuzhl@cib.ac.cn.
authors.forename: Yu-Chang
authors.initials: YC
authors.lastname: Liu
authors.forename: Yan
authors.initials: Y
authors.lastname: Liu
authors.forename: Zhong-Liu
authors.initials: ZL
authors.lastname: Wu
mesh_terms: D000429:Alcohol Oxidoreductases / Q000378:metabolism*; D055162:Biocatalysis; D004852:Epoxy Compounds / Q000737:chemistry / Q000378:metabolism*; D007700:Kinetics; D010105:Oxygenases / Q000378:metabolism*; D020005:Propanols / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D020005:Propanols; C006463:allyl alcohol; D000429:Alcohol Oxidoreductases; D010105:Oxygenases; C026721:styrene monooxygenase; C004312:glycidol