Photochemical generation and reactivity of the major hydroxyl radical adduct of thymidine. Academic Article uri icon


  • 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 -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.

published proceedings

  • Org Lett

author list (cited authors)

  • San Pedro, J., & Greenberg, M. M.

complete list of authors

  • San Pedro, Joanna Maria N||Greenberg, Marc M

publication date

  • June 2012