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 Jul 2016
Accepted
03 Oct 2016
First published
10 Oct 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

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