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%. This journal is
Original language | English |
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Pages (from-to) | 2146-2152 |
Number of pages | 7 |
Journal | ORGANIC AND BIOMOLECULAR CHEMISTRY |
Volume | 13 |
Issue number | 7 |
DOIs | |
Publication status | Published - 21 Feb 2015 |
MoE publication type | A1 Journal article-refereed |