Issue 2, 2017

Engineering a thermostable transketolase for arylated substrates

Abstract

Aromatic components are difficult substrates for enzymes catalyzing stereoselective carboligation reactions. We have engineered transketolase from Geobacillus stearothermophilus by directed evolution to utilize arylalkanals and benzaldehyde as the electrophilic substrate in highly stereoselective C–C bond forming conversions. Enzyme variants were discovered with rate accelerations up to 28-fold that convert 2-phenylethanal, 3-phenylpropanal, phenyloxyethanal, benzyloxyethanal, and (N-Cbz)-3-aminopropanal with formation of the corresponding aryl-substituted 1,3-dihydroxyketones in good yields (60–72%) and virtually complete (3S)-stereoselectivity (>99% ee). Novel double-site variants were also found for the conversion of benzaldehyde.

Graphical abstract: Engineering a thermostable transketolase for arylated substrates

Supplementary files

Article information

Article type
Paper
Submitted
22 7月 2016
Accepted
03 10月 2016
First published
10 10月 2016
This article is Open Access
Creative Commons BY-NC license

Green Chem., 2017,19, 481-489

Engineering a thermostable transketolase for arylated substrates

T. Saravanan, M. Reif, D. Yi, M. Lorillière, F. Charmantray, L. Hecquet and W. Fessner, Green Chem., 2017, 19, 481 DOI: 10.1039/C6GC02017H

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial 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