Synthesis of(S)-omeprazole catalyzed by soybean pod peroxidase in
water-in-oil microemulsions:optimization and modeling
Abstract
Response surface methodology(RSM)was used to optimize the oxidizing the
omeprazole sulfide to(S)-omeprazole catalyzed by soybean pod
peroxidase(SPP) in cetyltrimethylammonium bromide
(CTAB)/isooctane/n-butyl alcohol/water water-in-oil microemulsions. With
the initial concentration of SPP of 3200 U ml-1, the conversion of the
omeprazole sulfide, the (S)-omeprazole yield and ee were 93.75%,
91.56% and 96.08%, respectively. The mechanism of asymmetric
sulfoxidations catalyzed by SPP involves three concomitant mechanisms as
follows:(1) a two-electron reduction of SPP-I, (2) a single-electron
transfer to SPP-I and (3) nonenzymatic reactions. With 5.44% of the
average relative error, a kinetic model based on the mechanisms was
established, and the SPP-catalyzed reactions including both the
two-electron reduction and the single-electron transfer mechanisms obey
ping-pong mechanism with substrate and product inhibition, while
nonenzymatic reactions follow a power law. This study has also
demonstrated the feasibility of SPP as a substitute with low cost,
excellent enantioselectivity and better thermal stability.