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

GND
1190668750
Affiliation
Institute for Biochemistry, Biotechnology and Bioinformatics, Technische Universität Braunschweig
Leemans, Laura; van Langen, Luuk; Hollmann, Frank;
ORCID
0000-0002-6670-0574
Affiliation
Institute for Biochemistry, Biotechnology and Bioinformatics, Technische Universität Braunschweig
Schallmey, Anett

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.

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