Penicillin acylase-catalyzed acyl group transfer to amino acids, their esters and peptides: a kinetic study

Kinetics of penicillin acylase-catalyzed acyl group transfer to amino acids, their esters and peptides have been analyzed. The synthesized product accumulation curves have clearly expressed a maximum. Amino acids with non-branched side chain alkyl radicals were demonstrated to be effective nucleophiles, with glycine, L-phenylalanine and L-phenylglycine being the best. D-amino acids were shown to possess much lower reactivity. Practically for all L-amino acids and peptides tested, the yield of their N-phenylacetyl derivatives in the course of penicillin acylase-catalyzed acyl group transfer reactions was found to be more than 50%. Optimization of such enzymatic synthesis required to increase its potential on the preparative scale.