Photochemical generation and reactivity of the major hydroxyl radical adduct of thymidine |
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Authors: | San Pedro Joanna Maria N Greenberg Marc M |
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Institution: | Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA. |
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Abstract: | 5,6-Dihydro-5-hydroxythymidin-6-yl radical (1), the major reactive intermediate resulting from hydroxyl radical addition to C5 of the pyrimidine, is produced via 350 nm photolysis of a 2,5-dimethoxyphenylsulfide precursor (2). Competition between O(2) and thiol for 1 suggests that the radical reacts relatively slowly with β-mercaptoethanol compared to other alkyl radicals. Overall, aryl sulfide 2 should be an effective precursor for the major hydroxyl radical adduct of thymidine in DNA. |
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