Lipase-catalyzed condensation of p-methoxyphenethyl alcohol and carboxylic acids with different steric and electrical properties in acetonitrile.

The substrate selectivity of Candida antarctica lipase for various carboxylic acids was systematically investigated for their condensation with p-methoxyphenethyl alcohol in acetonitrile. The electron density of a carboxylic carbon and the projection area of an acid molecule were numerical indicators for evaluating the substrate selectivity. Both the electron density and projection area had an influence on the V/Km value, while only the projection area affected the Km value. The presence of conjugation with a carboxyl group in an acid and a branched structure in the non-carboxylic region independently lowered the V/Km value by an order of 1.