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Trapping a labile adduct formed between an ortho-quinone methide and 2'-deoxycytidine. 2011
Michael P McCrane, and
Emily E Weinert, and
Ying Lin, and
Eugene P Mazzola, and
Yiu-Fai Lam, and
Peter F Scholl, and
Steven E Rokita
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
Selective oxidation by bis[(trifluoroacetoxy)iodo]benzene (BTI) provides an effective trap for quenching adducts formed reversibly between dC and an ortho-quinone methide (QM) under physiological conditions. A model adduct generated by 4-methyl-o-QM and 2'-deoxycytidine is rapidly converted by intramolecular cyclization and loss of aromaticity to a characteristic product for quantifying QM alkylation. However, BTI induces a surprising rearrangement driven by overoxidation of a derivative lacking an alkyl substituent at the 4-position of the QM.
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