Issue 7, 2015

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%.

Graphical abstract: Synthesis of enantiopure glycidol derivatives via a one-pot two-step enzymatic cascade

Supplementary files

Article information

Article type
Paper
Submitted
15 Oct 2014
Accepted
08 Dec 2014
First published
08 Dec 2014

Org. Biomol. Chem., 2015,13, 2146-2152

Synthesis of enantiopure glycidol derivatives via a one-pot two-step enzymatic cascade

Y. Liu, Y. Liu and Z. Wu, Org. Biomol. Chem., 2015, 13, 2146 DOI: 10.1039/C4OB02186J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements