Bienzymatic cascade for the synthesis of an optically active O-benzoyl cyanohydrin

Laura Leemans, Luuk van Langen, Frank Hollmann, Anett Schallmey*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

5 Citations (Scopus)
75 Downloads (Pure)

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.

Original languageEnglish
Article number522
JournalCatalysts
Volume9
Issue number6
DOIs
Publication statusPublished - 2019

Keywords

  • Enantioselectivity
  • Enzyme cascade
  • Hydrocyanation
  • Hydroxynitrile lyase
  • Lipase
  • Transesterification

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