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

Leemans, Laura GND; van Langen, Luuk ORCID; Hollmann, Frank ORCID; Schallmey, Anett ORCID

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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Leemans, Laura / van Langen, Luuk / Hollmann, Frank / et al: Bienzymatic Cascade for the Synthesis of an Optically Active O-benzoyl Cyanohydrin. 2019. MDPI AG.

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