Photochemical generation and reactivity of the major hydroxyl radical adduct of thymidine.

Joanna Maria N San Pedro, Marc M Greenberg

Organic letters 2012 Jun 01

filter terms:

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.

Citation

Joanna Maria N San Pedro, Marc M Greenberg. Photochemical generation and reactivity of the major hydroxyl radical adduct of thymidine. Organic letters. 2012 Jun 01;14(11):2866-9