ENZYMATIC-SYNTHESIS OF (S)-IBUPROFEN ESTER PRODRUG FROM RACEMIC IBUPROFEN BY LIPASE IN ORGANIC-SOLVENTS

An enantioselective esterification process was developed for the direc t synthesis of (S)-ibuprofen ester prodrug from racemic ibuprofen by u sing 2-N-morpholinoethanol as an acyl acceptor and Candida rugosa lipa se as the biocatalyst in organic solvents. By selecting cyclohexane as the best reaction medium, the apparent fit of the specific initial ra te for (S)-ibuprofen and time-course conversions for both enantiomers supported the proposed reversible ping-pong Bi Bi enzymatic mechanism with a competitive inhibition by the alcohol. Moreover, the recovery a nd racemization of the remaining (R)-ibuprofen, as well as an investig ation of the present kinetic model applied to high substrate concentra tions, were reported.