Enantioselective microbial reduction of 1,1-dimethyl-1-sila-cyclohexan-2-one with growing cells of the yeast Kloeckera corticis (ATCC 20109)

Abstract

Abstract(R)-1,1-Dimethyl-1-sila-cyclohexan-2-ol [(R)-2] was prepared by enantioselective microbial reduction of 1,1-dimethyl-1-sila-cyclohexan-2-one (1) with growing cells of the yeast Kloeckera corticis (ATCC 20109). At a substrate concentration of 0.5 g/1 (temperature 27° C, incubation time 16 h), (R}-2 was obtained on a preparative scale in 60% yield and with an enantiomeric purity of 92% ee. Repeated recrystallization of the biotransformation product from n-hexane raised the enantiomeric purity to 99% ee.

Organosilicon Biotechnology

“…Cultures of K. corticis were successful in mediating the enantioselective reduction of 1,1-dimethyl-1-sila-cyclohexan-2-one to (R)-1,1-dimethyl-1-sila-cyclohexan-2-ol, in a 60% yield and 92% ee (Fig. 3) [46]. Recrystalization from n-hexane increased the enantiomeric excess to 98%.…”

“…4 Two biological steps and one chemical step afforded the diastereoselective reduction of rac-1-methyl-1-phenyl-1-sila-cyclohexan-2-one to (1S, 2R)-1-methyl-1-phenyl-1-sila-cyclohexan-2-ol [47] Fig. 3 The enantioselective reduction of 1,1-dimethyl-1-sila-cyclohexan-2-one by K. corticis cultures [46] As had been the case previously [35], the effect of increasing substrate concentration was deleterious to the catalytic efficiency of the organism. The Michaelis-Menten plots suggested that the optimal concentration of substrate was in the range of 0.1 mg/mL, however, in the opinion of the paper's authors, the reaction remained reasonably quick up to about 1.0 mg/mL substrate eliciting specific activity of 0.02 mmol/g/min compared to 0.06 mmol/g/min at 0.1 mg/mL [50].…”

Synthesis and enantioselective enzymatic hydrolysis of rac-dimethylphenyl[1-phenylacetamido)ethyl]silane

“…During our investigations on the synthesis of optically active organosilicon compounds by use of stereoselective biotransformations, both whole microbial cells [1][2][3][4][5][6] and free enzymes [7] were used as biocatalysts (for recent reviews see refs. [8][9][10].…”