Synthesis And Activity Of The Glutathione Analogue Gamma-(L-Gamma-Oxaglutamyl)-L-Cysteinyl-Glycine

An efficient synthesis of the backbone modified glutathione analogue gamma-(L-gamma-oxaglutamyl)-L-cysteinyl-glycine (7), characterized by the presence of an urethane O-CO-NH linkage replacing the gamma-glutamylic CH2CO-NH fragment is described. The new analogue has been fully characterized by H-1- and C-13-NMR and FAB-MS. Compound 7 was tested for inhibition of gamma-glutamyltransferase asl activity and was found to be a non-competitive inhibitor of hog kidney gamma-glutamyltransferase (EC 2.3.2.2).