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

abstract

• 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.

authors

• San Pedro, Joanna Maria

published proceedings

• Org Lett

author list (cited authors)

• San Pedro, J., & Greenberg, M. M.

citation count

• 13

complete list of authors

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

publication date

• June 2012

publisher

• American Chemical Society (ACS)  Publisher

published in

• Organic Letters  Journal

keywords

• DNA
• Hydroxyl Radical
• Molecular Structure
• Photochemical Processes
• Thymidine

PubMed Central ID

• 22616940

Digital Object Identifier (DOI)

• 10.1021/ol301109z

start page

• 2866

end page

• 2869

volume

• 14

issue

• 11

URL

• http://dx.doi.org/10.1021/ol301109z