Study of the removal of allyl esters by Candida antarctica lipase B (CAL-B) and pig liver esterase (PLE)

A number of allyl esters of various carboxylic acids and N-protected amino acids were synthesized and their hydrolysis by Candida antarctica lipase B and pig liver esterase was studied. In order to test the selectivity, the enzymatic hydrolysis of the corresponding methyl and ethyl esters was also examined. Both enzymes easily remove the allyl esters of monocarboxylates. The chemo- and regio-selectivity for the hydrolysis of glutamate diesters was studied, too, and it was found that the preference for the hydrolysis of a particular ester group depends not only on the ease of the hydrolysis observed for the esters of monocarboxylic acids, but also on the position (α- or γ-).