title: E.S.R. of spin-trapped radicals in aqueous solutions of pyrimidine nucleosides and nucleotides. Reactions of the hydroxyl radical.
abstract: Free radicals produced by the reactions of OH radicals with ribose phosphates, pyrimidine nucleosides and nucleotides in aqueous solutions have been investigated by e.s.r. and spin-trapping techniques. OH radicals were generated by U.V. -photolysis of hydrogen peroxide and short-lived free radicals of the samples were spin-trapped by t-nitrosobutane and identified by e.s.r. spectroscopy. For ribose-5'-phosphate and 2' -deoxyribose-5' -phosphate, e.s.r. spectra observed consisted mainly of singles due to -C(5')H2 radicals which were initiated by H-abstraction from the sugar at the C-4' position and formed by the radical transfer to the C-5' position. It has also been shown that OH radicals abstract a hydrogen atom from the sugar at C-1' and C-5' positions. For cytidine, deoxycytidine, 5'-CMP, 3' -CMP and 5' -dCMP, four radicals have been observed and for uridine, deoxyuridine, 5' -UMP, 3' -UMP and 5' -dUMP, the existence of at least three radical species have been established. In contrast to the case of ribose phosphates, no signals due to -C(5')H2 radicals were detected for pyrimidine nucleosides and nucleotides. The results are discussed in relation to a recent mechanism which described OH-induced strand breaks of DNA.
mesh_terms: D004578:Electron Spin Resonance Spectroscopy; D005609:Free Radicals; D006878:Hydroxides; D017665:Hydroxyl Radical; D011741:Pyrimidine Nucleosides; D011742:Pyrimidine Nucleotides; D012996:Solutions; D014867:Water
chemical_list: D005609:Free Radicals; D006878:Hydroxides; D011741:Pyrimidine Nucleosides; D011742:Pyrimidine Nucleotides; D012996:Solutions; D014867:Water; D017665:Hydroxyl Radical