Journal of the Chemical Society. Perkin transactions II p. 1117 - 1122 (1988)
Update date:2022-08-03
Topics:
Eriksen, Trygve
Fransson, Gunilla
The .OH-induced oxidation of glutathione in basic aqueous solution has been found to produce the sulphur-centred radical GS. (GSSG.- and two reducing radicals.Decarboxylation, considered to be initiated by .OH radical addition to the nitrogen of the amino group on the γ-glutamyl unit, was found to be effective for methylated glutathione (GSMe) and ophthalmic acid (GMe) but of minor importance for glutathione.The G-values for the strongly reducing α-amino radicals formed on decarboxylation were found to be 3.3, 3.3, and 0.5 for GSMe, GME, and GSH, respectively, at pH 10.5.The formation of an additional strongly reducing radical with G=2.2 at pH 10.5 was demonstrated by measuring the electron-transfer to p-nitroacetophenone (PNAP).This radical is not formed from GSMe or GMe.We suggest that the underlying mechanism for the formation of this species is based on pH-dependent conformational changes of glutathione followed by .OH addition to the cysteine sulphur, or hydrogen abstraction from the CH2 group in the α-position to the sulphur leading to the formation of a reducing carbon-centred radical.
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