title: Photochemical generation and reactivity of the major hydroxyl radical adduct of thymidine.
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.
authors.affiliation: Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA.
authors.forename: Joanna Maria N
authors.initials: JM
authors.lastname: San Pedro
authors.forename: Marc M
authors.initials: MM
authors.lastname: Greenberg
mesh_terms: D004247:DNA / Q000737:chemistry; D017665:Hydroxyl Radical / Q000737:chemistry*; D015394:Molecular Structure; D055668:Photochemical Processes; D013936:Thymidine / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: C574681:5,6-dihydro-5-hydroxythymidin-6-yl radical; D017665:Hydroxyl Radical; D004247:DNA; D013936:Thymidine