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 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).
Calcagni
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A
Dipartimento di Studi Farmaceutici, Università La Sapienza, Roma, Italy.
Duprè
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S
Lucente
G
G
Luisi
G
G
Pinnen
F
F
Rossi
D
D
Spirito
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A
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*
D004791:Enzyme Inhibitors; C104034:gamma-oxaglutamyl-cysteinyl-glycine; D005723:gamma-Glutamyltransferase; D005978:Glutathione