The efficient anti-Prelog asymmetric reduction of prochiral ketones with Acetobacter pasteurianus GIM1.158 cells was successfully conducted using deep eutectic solvents (DES) as reaction media. A variety of DES were prepared by mixing cholinium chloride with various hydrogen band donors and tested for their potentials for the bioreduction of 2-octanone to (R)-2-octanol. Diverse DES exerted different effects on the reaction. The best results were observed with the mixture of  cholinium chloride and ethylene glycol ([CC][EG]) at a concentration of 60% (v/v), due to its better biocompatibility. Under the optimal conditions (35 oC, pH 5.0, 500 mM isopropanol, 50 mM 2-octanone) for the bioreduction in [CC][EG]-containing system, the yield increased significantly from 81%  (aqueous buffer) to 92% and the product e.e. kept above 99.9%. Additionally, the efficient biocatalytic process with Acetobacter pasteurianus GIM1.158 and [CC][EG] was feasible on a 500-mL preparative scale and  showed to very promising for synthesis of  (R)-2-octanol.

Use of deep eutectic solvents to prompt biocatalytic  asymmetric reduction of prochiral ketones with Acetobacter pasteurianus GIM1.158 cells

248th National Meeting (2014)

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