cysteinyldopa and dopachrome

Human glutathione transferase M2-2 prevents the formation of neurotoxic aminochrome and dopachrome by catalyzing the conjugation of dopamine and dopa o-quinone with glutathione. NMR analysis of dopamine and dopa o-quinone-glutathione conjugates revealed that the addition of glutathione was at C-5 to form 5-S-glutathionyl-dopamine and 5-S-glutathionyl-dopa, respectively. Both conjugates were found to be resistant to oxidation by biological oxidizing agents such as O(2), H(2)O(2), and O(*-)(2), and the glutathione transferase-catalyzed reaction can therefore serve a neuroprotective antioxidant function.

Topics: Benzoquinones; Cysteinyldopa; Dihydroxyphenylalanine; Dopamine; Glutathione; Glutathione Transferase; Humans; Indolequinones; Indoles; Isoenzymes; Magnetic Resonance Spectroscopy; Models, Chemical; Oxidation-Reduction; Protein Binding; Quinones; Time Factors