S. Amrutkar, Linga Banoth, U. Banerjee
Jun 19, 2013
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0
Influential Citations
13
Citations
Journal
Tetrahedron Letters
Abstract
R)-1-(1-Naphthyl)ethanol is an essential chiral substrate for the synthesis of nonactin and dihydro-(1H)- quinoline-2-one derivatives. Stereoinversion of (S)-1-(1-naphthyl)ethanol to (R)-1-(1-naphthyl)ethanol by whole cell biocatalysis, using Candida parapsilosis, is reported here. Candida parapsilosis possesses a requisite redox system for the stereoinversion of secondary alcohol. The reaction conditions (tempera- ture, time, pH, organic solvent, etc.) significantly influenced the stereoinversion process. Optimum con- ditions were found to be the reaction temperature of 30 C, a cellmass concentration of 200 mg/mL, pH 7 (phosphate buffer, 50 mM), a shaking speed of 200 rpm, and a 12 h reaction time. Under these optimum conditions, (R)-1-(1-naphthyl)ethanol was obtained in 100% eeR and 88% yield.