ANALYSIS OF A LIPASE-CATALYZED KINETIC RESOLUTION BY CHIRAL NORMAL-PHASE LIQUID-CHROMATOGRAPHY

As part of our investigation of structure-activity relationships in a Candida rugosa lipase-catalyzed ester hydrolysis reaction, methyl 2-(o ctylsulfinyl)benzoate has been studied, with respect to rate and enant ioselectivity behaviour, using two different lipase preparations, A ch iral normal-phase liquid chromatography method has been developed for determination of the experimental data, degree of conversion (c) and e nantiomeric excess of the substrate (ee(s)) or the product (ee(p)), ne eded for calculation of the enantioselectivity in a kinetic resolution of this kind, A recently developed new class of network-polymeric chi ral stationary phases, giving baseline-resolution with high selectivit ies for the ester substrates as well as their corresponding carboxylic acid products, permits, without any derivatization, an accurate and d irect determination of the rate of the hydrolysis reaction and of the enantioselectivity from one and the same chromatogram. (C) 1997 by Joh n Wiley & Sons, Ltd.