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

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 subse...

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Bibliographic Details
Published in:Catalysts
Main Authors: Laura Leemans, Luuk van Langen, Frank Hollmann, Anett Schallmey
Format: Article in Journal/Newspaper
Language:English
Published: MDPI AG 2019
Subjects:
Enantioselectivity
enzyme cascade
hydroxynitrile lyase
lipase
hydrocyanation
transesterification
Chemical technology
TP1-1185
Chemistry
QD1-999
Antarc*
Antarctica
Online Access:https://doi.org/10.3390/catal9060522
https://doaj.org/article/bb0b0d7c038d4942ae494d2d35170ab7
Description
Summary: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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