TY - JOUR
T1 - DNA cleavage by the photolysis of cyclopentadienyl metal complexes
T2 - Mechanistic studies and sequence selectivity of strand scission by CpW(CO) 3CH3
AU - Mohler, Debra L.
AU - Downs, Jennifer R.
AU - Hurley-Predecki, Allison L.
AU - Sallman, Jennifer R.
AU - Gannett, Peter M.
AU - Shi, Xianglin
PY - 2005/11/11
Y1 - 2005/11/11
N2 - The photolysis of CpW(CO)3Me has been shown to produce methyl radicals and to cleave DNA in a single-stranded manner, and preliminary evidence implicated a carbon-centered radical in this process. In this work, the mechanism of strand scission in this reaction was determined to occur by hydrogen atom abstraction from the 4′- and 5′-positions of the deoxyribose moiety of the backbone of DNA. Additionally, in a side reaction that does not lead to frank strand scission, all four bases of DNA are methylated under these conditions; however, none of these base or backbone modifications lead to the formation of abasic sites.
AB - The photolysis of CpW(CO)3Me has been shown to produce methyl radicals and to cleave DNA in a single-stranded manner, and preliminary evidence implicated a carbon-centered radical in this process. In this work, the mechanism of strand scission in this reaction was determined to occur by hydrogen atom abstraction from the 4′- and 5′-positions of the deoxyribose moiety of the backbone of DNA. Additionally, in a side reaction that does not lead to frank strand scission, all four bases of DNA are methylated under these conditions; however, none of these base or backbone modifications lead to the formation of abasic sites.
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U2 - 10.1021/jo050338h
DO - 10.1021/jo050338h
M3 - Article
C2 - 16268578
AN - SCOPUS:27744480112
SN - 0022-3263
VL - 70
SP - 9093
EP - 9102
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 23
ER -