Mass transfer limitation as a tool to enhance the enantiomeric excess in the enzymatic synthesis of chiral cyanohydrins

Pieter Jan Gerrits, Wouter F. Willeman, Adrie J.J. Straathof, Joseph J. Heijnen, Johannes Brussee, Arne Van Der Gen

Research output: Contribution to journalArticleScientificpeer-review

35 Citations (Scopus)

Abstract

The enantioselective synthesis of cyanohydrins catalyzed by R-hydroxynitrile lyase in an aqueous-organic liquid two-phase system using, mass transfer limitation to enhance enantiomeric excess at 5°C and pH 5.5 is described. Benzaldehyde, a good substrate, and cinnamaldehyde, a notoriously difficult substrate, were used as model substrates and compared in order to establish the mass transfer limitation concept in a two-liquid phase system, where the non-enzymatic-racemic reaction competes. Enzyme concentration and phase volume ratio between organic and buffer phase were geared to one another to enhance the enantiomeric excess for each substrate. In both cases, after optimization, excellent chemical conversion (>99% on a 60mmol scale), high throughput and high enantiomeric excess (benzaldehyde >99% and cinnamaldehyde >96%) were achieved.

Original languageEnglish
Pages (from-to)111-121
JournalJournal of Molecular Catalysis B: Enzymatic
Volume15
Issue number4-6
DOIs
Publication statusPublished - 2001

Keywords

  • Cyanohydrins
  • HCN
  • Mass transfer limitation model
  • Mass transfer limiting enzyme concentration
  • R-hydroxynitrile lyase

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