Immobilisation of different <i>Candida rugosa</i> lipases by adsorption onto polypropylene powder: application to chiral synthesis of ibuprofen and <i>trans</i>‐2‐phenyl‐1‐cyclohexanol esters

Abstract

Abstract Candida rugosa lipases (CRLs) were immobilised by adsorption onto a commercial polypropylene powder EP100™. Two commercial CRLs from Sigma and Amano were used together with two CRLs obtained by fed‐batch fermentation using oleic acid as a carbon source (UAB‐CRL). Significant differences were observed in the isotherm adsorption patterns for the commercial and fermented lipases, probably caused by differences in their polysaccharide content. The commercial lipases showed a classical Langmuir adsorption pattern, whereas fed‐batch produced lipases with high polysaccharide content tended to conform to a BET multilayer adsorption equation. Immobilised CRLs also showed different behaviour in the resolution of two interesting pharmaceutical products: ibuprofen and trans ‐2‐phenyl‐1‐cyclohexanol (TPCH) in the enantioselective esterification reaction in organic media. In the case of ibuprofen, CRLs showed important differences in terms of esterification rate, probably due to diffusional limitation effects caused by the high polysaccharide content present in UAB‐CRLs. In the case of TPCH, however, polysaccharide content did not appear to influence the esterification rate. A high enantioselective esterification was observed for all CRLs tested in the resolution of both products. © 2002 Society of Chemical Industry