REGIOSELECTIVITY AND ENANTIOSELECTIVITY OF THE CANDIDA-ANTARCTICA LIPASE-CATALYZED AMIDATIONS OF CBZ-L-GLUTAMIC AND CBZ-D-GLUTAMIC ACID DIESTERS

Candida antarctica lipase (CAL) catalyzed amidation of Cbz-glutamic ac id diesters takes place in a regioselective way to give the correspond ing monoamide derivatives. The regioselectivity was found to be depend ent on the reacting Glu enantiomer. Thus, amidations of Cbz-L-Glu dies ters regiospecifically afforded alpha-amide while the gamma-ester is s electively substituted in the D-enantiomer. This enzymatic reaction al so shows enantioselectivity when a chiral amine is used as nucleophile .