title: Trapping a labile adduct formed between an ortho-quinone methide and 2'-deoxycytidine.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
authors.forename: Michael P
authors.initials: MP
authors.lastname: McCrane
authors.forename: Emily E
authors.initials: EE
authors.lastname: Weinert
authors.forename: Ying
authors.initials: Y
authors.lastname: Lin
authors.forename: Eugene P
authors.initials: EP
authors.lastname: Mazzola
authors.forename: Yiu-Fai
authors.initials: YF
authors.lastname: Lam
authors.forename: Peter F
authors.initials: PF
authors.lastname: Scholl
authors.forename: Steven E
authors.initials: SE
authors.lastname: Rokita
mesh_terms: D000478:Alkylation; D003841:Deoxycytidine / Q000737:chemistry*; D045563:Indolequinones / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D045563:Indolequinones; D003841:Deoxycytidine; C068040:quinone methide