Effect of ionic liquid [BMIM][PF6] on asymmetric reduction of ethyl 2-oxo-4-phenylbutyrate by Saccharomyces cerevisiae.
The effect of ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIM][PF6]) on the asymmetric reduction of ethyl 2-oxo-4-phenylbutyrate (EOPB) to synthesize optical active ethyl 2-hydroxy-4-phenylbutyrate (EHPB) catalyzed by Saccharomyces cerevisiae was investigated. (R)-EHPB [70.4%, e.e.(R)] is obtained using ethyl ether or benzene as the solvent. The main product is (S)-EHPB [27.7%, e.e.(S)] in [BMIM][PF6]. However, in ionic liquid-water (10:1, v/v) biphasic system, the enantioselectivity of the reduction is shifted towards (R)-side, and e.e.(R) is increased from 6.6 to 82.5% with the addition of ethanol (1%, v/v). The effect of the use of [BMIM][PF6] as an additive in relatively small amounts on the reduction was also studied. We find that there is a decline in the enantioselectivity of the reduction in benzene. In addition, a decrease in the conversion of EOPB and the yield of EHPB with increasing [BMIM][PF6] concentrations occurs in either organic solvent-water biphasic systems or benzene.
Shi
Yu-Gang
YG
School of Chemical and Material Engineering, Jiangnan University, 1800 Lihu Road, 214122, Wuxi, Jiangsu, China.
Fang
Yun
Y
Ren
Yue-Ping
YP
Wu
Hong-Ping
HP
Guan
Hui-Lei
HL
D007093:Imidazoles / Q000378:metabolism*; D052578:Ionic Liquids / Q000378:metabolism*; D010084:Oxidation-Reduction; D010654:Phenylbutyrates / Q000378:metabolism*; D012441:Saccharomyces cerevisiae / Q000378:metabolism*
C412621:1-butyl-3-methylimidazolium hexafluorophosphate; D007093:Imidazoles; D052578:Ionic Liquids; D010654:Phenylbutyrates