Optimization and kinetic modeling of lipase mediated enantioselective kinetic resolution of (±)-2-octanol

Abstract

Chiral 2-octanol is one of the key intermediates for preparation of liquid crystal materials, as well as many optically active pharmaceuticals. Li-pase catalyzed kinetic resolution has proved to be an efficient technique for synthesis of enan-tiomerically enriched compounds. In the present study, optimization and kinetic modeling of ki-netic resolution of (±)-2-octanol was done by using vinyl acetate as an acyl donor in n-hep-tane as a solvent. Response surface methodol-ogy (RSM) and four-factor-five-level Centre Com-posite Rotatable Design (CCRD) were employed to evaluate the effect of various parameters such as speed of agitation, enzyme loading, tempera-ture and acyl donor/alcohol molar ratio on con-version, enantiomeric excess (ee), enantioselec-tivity and initial rate of reaction. Acylation of 2-octanol with vinyl acetate catalyzed by Novozyme 435 follows the ternary complex mechanism (ordered bi-bi mechanism) with inhibition by 2-octanol.