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PHOTOCHEMICAL ADDITION OF GLUTATHIONE TO URACIL AND THYMINE
Author(s) -
Varghese A. J.
Publication year - 1974
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1974.tb06585.x
Subject(s) - glutathione , uracil , thymine , chemistry , adduct , cysteine , pyrimidine , photochemistry , stereochemistry , biochemistry , organic chemistry , dna , enzyme
—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.