Efficient asymmetric reduction of 4-(trimethylsilyl)-3-butyn-2-one by Candida parapsilosis cells in an ionic liquid-containing system.
Hydrophilic ionic liquids (ILs) were employed as green solvents to construct an IL-containing co-solvent system for improving the asymmetric reduction of 4-(trimethylsilyl)-3-butyn-2-one by immobilized Candida parapsilosis cells. Among 14 hydrophilic ILs examined, 1-(2'-hydroxyl)ethyl-3-methylimidazolium nitrate (C(2)OHMIM·NO(3)) was considered as the most suitable IL for the bioreduction with the fastest initial reaction rate, the highest yield and the highest product e.e., which may be due to the good biocompatibility with the cells. For a better understanding of the bioreduction performed in the C(2)OHMIM·NO(3)-containing co-solvent system, the effects of several crucial variables were systematically investigated. The optimal C(2)OHMIM·NO(3) content, substrate concentration, buffer pH, co-substrate concentration and temperature were 10% (v/v), 3.0 mmol/L, 5.0, 98.1 mmol/L and 30°C, respectively. Under the optimal conditions, the initial reaction rate, the maximum yield and the product e.e. were 17.3 µmol/h g(cell), 95.2% and >99.9%, respectively, which are much better than the corresponding results previously reported. Moreover, the immobilized cells remained more than 83% of their initial activity even after being used repeatedly for 10 batches in the C(2)OHMIM·NO(3)-containing system, exhibiting excellent operational stability.
State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou, People's Republic of China.
Bo-Bo
BB
Zhang
Wen-Yong
WY
Lou
Wen-Jing
WJ
Chen
Min-Hua
MH
Zong
D002074:Butanones / Q000378:metabolism*; D002175:Candida / Q000378:metabolism*; D018914:Cells, Immobilized / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D057927:Hydrophobic and Hydrophilic Interactions; D052578:Ionic Liquids / Q000737:chemistry*; D010084:Oxidation-Reduction; D012997:Solvents / Q000737:chemistry*; D013696:Temperature; D014297:Trimethylsilyl Compounds / Q000378:metabolism*
C576730:4-(trimethylsilyl)-3-butyn-2-one; D002074:Butanones; D052578:Ionic Liquids; D012997:Solvents; D014297:Trimethylsilyl Compounds