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

Catalysts

Frank Hollmann¹  Anett Schallmey²  Laura Leemans²  Luuk van Langen³ 

[1] Department of Biotechnology, Delft University of Technology, Van der Maasweg 9, 2629 HZ Delft, The Netherlands;Institute for Biochemistry, Biotechnology and Bioinformatics, Technische Universität Braunschweig, Spielmannstr. 7, 38106 Braunschweig, Germany;Viazym B.V., Molengraaffsingel 10, 2629 JD Delft, The Netherlands;

关键词: Enantioselectivity;    enzyme cascade;    hydroxynitrile lyase;    lipase;    hydrocyanation;    transesterification;   

DOI  :  10.3390/catal9060522

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown