Esterification in non-aqueous media: Activity and selectivity of porcine pancreas carboxylesterase depending on the structure of the alcoholic substrate

Article abstract of DOI:10.1016/S0957-4166(00)80444-9

Enzymatic esterification in n-hexane was carried out using various unsaturated and aromatic (R,S)-alcohols, dodecanoic acid and a crude pancreatic extract. A 'model' was developed describing reactivity and selectivity of the enzymatic catalysis. These parameters were found to depend on the structural features of the side chains at the reactive chiral center. In several homologous series of substrates reversal of configuration of the preferred enantiomer was observed. The evaluated 'model' will be a helpful tool to establish future synthetic strategies.