TY - JOUR
T1 - Mass transfer limitation as a tool to enhance the enantiomeric excess in the enzymatic synthesis of chiral cyanohydrins
AU - Gerrits, Pieter Jan
AU - Willeman, Wouter F.
AU - Straathof, Adrie J.J.
AU - Heijnen, Joseph J.
AU - Brussee, Johannes
AU - Van Der Gen, Arne
PY - 2001
Y1 - 2001
N2 - 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.
AB - 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.
KW - Cyanohydrins
KW - HCN
KW - Mass transfer limitation model
KW - Mass transfer limiting enzyme concentration
KW - R-hydroxynitrile lyase
UR - http://www.scopus.com/inward/record.url?scp=0035501535&partnerID=8YFLogxK
U2 - 10.1016/S1381-1177(01)00014-5
DO - 10.1016/S1381-1177(01)00014-5
M3 - Article
AN - SCOPUS:0035501535
SN - 1381-1177
VL - 15
SP - 111
EP - 121
JO - Journal of Molecular Catalysis B: Enzymatic
JF - Journal of Molecular Catalysis B: Enzymatic
IS - 4-6
ER -