Interaction of L-gamma-glutamyl-alpha,beta-dehydroamino acids with gamma-glutamyl transpeptidase.
Three gamma-glutamyl alpha,beta-dehydroamino acids: L-gamma-glutamyl-dehydroalanine, L-gamma-glutamyl-(Z)-dehydrobutyrine and L-gamma-glutamyl-(E)-dehydrobutyrine have been prepared as potential ligands (inhibitors or substrates) for gamma-glutamyl transpeptidase (GGT). Both isomers of gamma-glutamyl-dehydrobutyrines proved to be inhibitors of GGT, slightly better than the saturated analogue, L-gamma-glutamyl-L-butyrine. However, their solvolysis catalysed by the enzyme is slower than that of the latter. L-gamma-Glutamyl-(E)-dehydrobutyrine seems to be a more active compound in both enzymatic tests. L-gamma-Glutamyl-dehydroalanine elicited only low inhibitory activity and, moreover, was unstable under conditions of the solvolysis test.
Kubica
Z
Z
Department of Organic Chemistry, University of Opole, Poland.
Rzeszotarska
B
B
Midura-Nowaczek
K
K
Roszkowska-Jakimiec
W
W
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D012997:Solvents; D005723:gamma-Glutamyltransferase / Q000037:antagonists & inhibitors*
D004791:Enzyme Inhibitors; D012997:Solvents; D005723:gamma-Glutamyltransferase