Trapping a labile adduct formed between an ortho -quinone methide and 2′-deoxycytidine

Michael P. McCrane, Emily Weinert, Ying Lin, Eugene P. Mazzola, Yiu Fai Lam, Peter F. Scholl, Steven E. Rokita

Research output: Contribution to journalArticle

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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.(Figure Presented)

Original languageEnglish (US)
Pages (from-to)1186-1189
Number of pages4
JournalOrganic Letters
Volume13
Issue number5
DOIs
Publication statusPublished - Mar 4 2011

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

McCrane, M. P., Weinert, E., Lin, Y., Mazzola, E. P., Lam, Y. F., Scholl, P. F., & Rokita, S. E. (2011). Trapping a labile adduct formed between an ortho -quinone methide and 2′-deoxycytidine. Organic Letters, 13(5), 1186-1189. https://doi.org/10.1021/ol200071p