Regioselective lipase-catalyzed synthesis of L-glutamic α-monoamide derivatives. Effect of the N-blocking group

Article abstract of DOI:10.1016/S0040-4020(97)00741-2

Several Block-L-Glu(OEt)-OEt (Block = amides, carbamates and trityl group) have been subjected to an aminolysis reaction catalyzed by the lipase B of Candida antarctica. The reaction took place in a regioselcctive manner and α-monoamides were obtained in all cases (except the bulky trityl group that did not react). Besides (he synthetic value of the method, the results may empirically point out to some features of tile active site of the enzyme as the reaction rate was severely affected by volume and electronic characteristics of the blocking group.