PHOTOCHEMICAL ADDITION OF GLUTATHIONE TO URACIL AND THYMINE

Abstract —Irradiation (Λ > 240 nm) of thymine in aqueous solution in the presence of glutathione produces primarily 5-S-glutathione-5, 6-dihydropyrimidine and 5- S, S -glutathione-5, 6-dihydro-pyrimidine. These adducts are obtained in better yields when the irradiations (Λ > 280 nm) are carried out in the presence of triplet-state sensitizers. Reduction of 5- S, S -glutathione-5, 6-dihydropyrimidine with zinc dust in acetic acid yields the corresponding 5, 6-dihydropyrimidine. When thymine-glutathione adducts are heated in 6 N HCl for 2h, 5- S -cysteine-5, 6-dihydrothymine and 5- S, S -cysteine-5, 6-dihydrothymine are formed. Under these conditions, uracil-glutathione adducts are less stable and are converted to products other than uracil-cysteine adducts.