title: Penicillin acylase-catalyzed acyl group transfer to amino acids, their esters and peptides: a kinetic study.
abstract: 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.
authors.affiliation: A.N. Belozersky Institute of Physico-Chemical Biology, Moscow State University, USSR.
authors.forename: R J
authors.initials: RJ
authors.lastname: Didziapetris
authors.forename: V K
authors.initials: VK
authors.lastname: Svedas
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D002384:Catalysis; D004926:Escherichia coli / Q000201:enzymology; D004952:Esters / Q000737:chemistry; D007700:Kinetics; D010399:Penicillin Amidase / Q000737:chemistry* / Q000378:metabolism; D010455:Peptides / Q000737:chemistry
chemical_list: D000596:Amino Acids; D004952:Esters; D010455:Peptides; D010399:Penicillin Amidase