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  • Title: 5,6-Dihydropyrimidine peroxyl radical reactivity in DNA.
    Author: San Pedro JM, Greenberg MM.
    Journal: J Am Chem Soc; 2014 Mar 12; 136(10):3928-36. PubMed ID: 24579910.
    Abstract:
    Nucleobase radicals are a major family of reactive species produced in DNA as a result of oxidative stress. Two such radicals, 5-hydroxy-5,6-dihydrothymidin-6-yl radical (1) and 5,6-dihydrouridin-6-yl radical (5), were independently generated within chemically synthesized oligonucleotides from photochemical precursors. Neither nucleobase radical produces direct strand breaks or alkali-labile lesions in single or double stranded DNA. The respective peroxyl radicals, resulting from O2 trapping, add to 5'-adjacent nucleobases, with a preference for dG. Distal dG's are also oxidatively damaged by the peroxyl radicals. Experiments using a variety of sequences indicate that distal damage occurs via covalent modification of the 5'-adjacent dG, but there is no evidence for electron transfer by the nucleobase peroxyl radicals.
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