title: Synthesis and activity of the glutathione analogue gamma-(L-gamma-oxaglutamyl)-L-cysteinyl-glycine.
abstract: 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 1H- and 13C-NMR, and FAB-MS. Compound 7 was tested for inhibition of gamma-glutamyl-transferase activity and was found to be a non-competitive inhibitor of hog kidney gamma-glutamyltransferase (EC 2.3.2.2).
authors.affiliation: Dipartimento di Studi Farmaceutici, Università La Sapienza, Roma, Italy.
authors.forename: A
authors.initials: A
authors.lastname: Calcagni
authors.forename: S
authors.initials: S
authors.lastname: Duprè
authors.forename: G
authors.initials: G
authors.lastname: Lucente
authors.forename: G
authors.initials: G
authors.lastname: Luisi
authors.forename: F
authors.initials: F
authors.lastname: Pinnen
authors.forename: D
authors.initials: D
authors.lastname: Rossi
authors.forename: A
authors.initials: A
authors.lastname: Spirito
mesh_terms: D000818:Animals; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005978:Glutathione / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013552:Swine; D005723:gamma-Glutamyltransferase / Q000037:antagonists & inhibitors*
chemical_list: D004791:Enzyme Inhibitors; C104034:gamma-oxaglutamyl-cysteinyl-glycine; D005723:gamma-Glutamyltransferase; D005978:Glutathione