Conformation and proton configuration of pyrimidine deoxynucleoside oxidation damage products in water

Christopher J. La Francois, Yun Hee Jang, Tahir Cagin, William A. Goddard, Lawrence C. Sowers

Research output: Contribution to journalArticle

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Emerging data strongly suggest that the oxidation of DNA bases can contribute to genomic instability. Structural changes to DNA, induced by base oxidation, may reduce the fidelity of DNA replication and interfere with sequence-specific DNA-protein interactions. We have examined the structures of a series of pyrimidine deoxynucleoside oxidation damage products in aqueous solution. The modified nucleosides studied include the deoxynucleoside derivatives of 5-hydroxyuracil, 5-hydroxycytosine, 5- (hydroxymethyl)uracil, 5-(hydroxymethyl)cytosine, 5-formyluracil, and 5- formylcytosine. The influence of base oxidation on ionization constants, sugar conformation, and tautomeric configuration has been determined on the basis of UV, proton, and nitrogen NMR spectra of the 15N-enriched derivatives. The potential biological consequences of the structural perturbations resulting from base oxidation are discussed.

Original languageEnglish (US)
Pages (from-to)462-470
Number of pages9
JournalChemical Research in Toxicology
Issue number6
StatePublished - Jun 1 2000


ASJC Scopus subject areas

  • Toxicology

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