Synthesis of enantiopure glycidol derivatives via a one-pot two-step enzymatic cascade. Issue 7 (22nd December 2014)

• Record Type: Journal Article
• Authors: Liu, Yu-Chang; Liu, Yan; Wu, Zhong-Liu
• Is Part Of: Organic & biomolecular chemistry. Volume 13:Issue 7(2015)
• Page Start: 2146
• Page End: 2152
• Publication Date: 2014-12-22
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c4ob02186j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An enzymatic cascade reaction employing an S -specific ketoreductase and a styrene monooxygenase to synthesize enantiopure glycidol derivatives is described. 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 Ch KRED03 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%.