291525-23-0Relevant articles and documents
Independent Generation and Reactivity of 2′-Deoxy-5-methyleneuridin-5-yl, a Significant Reactive Intermediate Produced from Thymidine as a Result of Oxidative Stress
Anderson, Aaron S.,Hwang, Jae-Taeg,Greenberg, Marc M.
, p. 4648 - 4654 (2007/10/03)
2′-Deoxy-5-methyleneuridin-5-yl (1) is produced in a variety of DNA damage processes and is believed to result in the formation of lesions that are mutagenic and refractory to enzymatic repair. 2′-Deoxy-5-methyleneuridin-5-yl (1) was independently generated under anaerobic conditions via Norrish Type I photocleavage during Pyrex filtered photolysis of the benzyl ketone 7. The radical (1) exhibits behavior consistent with that of a resonance-stabilized radical. The KIE for hydrogen atom transfer from t-BuSH was found to be 7.3 ± 1.7. Competition studies between radical recombination and hydrogen atom donors (2,5-dimethyltetrahydrofuran, kTrap = 46.1 ± 15.4 M-1 s-1; propan-2-ol, kTrap = 13.6 ± 3.5 M-1 s-1) chosen to mimic the carbohydrate components of 2′-deoxyribonucleotides suggest that 2′-deoxy-5-methyleneuridin-5-yl (1) may be able to transfer damage from the nucleobase to the deoxyribose of an adjacent nucleotide in DNA under hypoxic conditions.