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Bienzymatic Cascade for the Synthesis of an Optically Active O-benzoyl Cyanohydrin

1
Institute for Biochemistry, Biotechnology and Bioinformatics, Technische Universität Braunschweig, Spielmannstr. 7, 38106 Braunschweig, Germany
2
Viazym B.V., Molengraaffsingel 10, 2629 JD Delft, The Netherlands
3
Department of Biotechnology, Delft University of Technology, Van der Maasweg 9, 2629 HZ Delft, The Netherlands
*
Author to whom correspondence should be addressed.
Catalysts 2019, 9(6), 522; https://doi.org/10.3390/catal9060522
Received: 14 May 2019 / Revised: 6 June 2019 / Accepted: 10 June 2019 / Published: 12 June 2019
(This article belongs to the Special Issue Biocatalysis: Chemical Biosynthesis)
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Abstract

A concurrent bienzymatic cascade for the synthesis of optically pure (S)-4-methoxymandelonitrile benzoate ((S)-3) starting from 4-anisaldehyde (1) has been developed. The cascade involves an enantioselective Manihot esculenta hydroxynitrile lyase-catalyzed hydrocyanation of 1, and the subsequent benzoylation of the resulting cyanohydrin (S)-2 catalyzed by Candida antarctica lipase A in organic solvent. To accomplish this new direct synthesis of the protected enantiopure cyanohydrin, both enzymes were immobilized and each biocatalytic step was studied separately in search for a window of compatibility. In addition, potential cross-interactions between the two reactions were identified. Optimization of the cascade resulted in 81% conversion of the aldehyde to the corresponding benzoyl cyanohydrin with 98% enantiomeric excess. View Full-Text
Keywords: Enantioselectivity; enzyme cascade; hydroxynitrile lyase; lipase; hydrocyanation; transesterification Enantioselectivity; enzyme cascade; hydroxynitrile lyase; lipase; hydrocyanation; transesterification
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Leemans, L.; van Langen, L.; Hollmann, F.; Schallmey, A. Bienzymatic Cascade for the Synthesis of an Optically Active O-benzoyl Cyanohydrin. Catalysts 2019, 9, 522.

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