Optical resolution of (R, S)-ibuprofen in organic solvent by porcine pancreatic lipase catalyzed enantioselective esterification

Abstract

Porcine pancreatic lipase (PPL), a comparatively inexpensive enzyme, was used in the optical resolution of (R, S)-ibuprofen in methanol through enantioselective esterification. The different reaction parameters during the esterification of (R, S)-ibuprofen using PPL was studied with respect to temperature, time, enzyme concentration, substrate concentration and water content. The percentage conversion initially was 13%, which increased to 33% after optimization of the different reaction conditions. Surfactant coating of PPL resulted in a 2.5-fold increase in the hydrolytic activity of PPL. Surfactant coated PPL, when used in the esterification reaction slightly increased the percentage conversion from 21 to 22.5%. In all the reactions, PPL showed preference for catalyzing the esterification of S-(+)-ibuprofen.