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Issue 2, 2017
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Engineering a thermostable transketolase for arylated substrates

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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

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Publication details

The article was received on 22 Jul 2016, accepted on 03 Oct 2016, published on 10 Oct 2016 and first published online on 10 Oct 2016


Article type: Paper
DOI: 10.1039/C6GC02017H
Citation: Green Chem., 2017,19, 481-489
  • Open access: Creative Commons BY-NC license
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    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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