Conformation and Proton Configuration of Pyrimidine Deoxynucleoside Oxidation Damage Products in Water
- 27 May 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in Chemical Research in Toxicology
- Vol. 13 (6) , 462-470
- https://doi.org/10.1021/tx990209u
Abstract
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 N-15-enriched derivatives. The potential biological. consequences of the structural perturbations resulting from base oxidation are discussed.This publication has 26 references indexed in Scilit:
- Photosensitized Oxidation of 5-Methyl-2‘-deoxycytidine by 2-Methyl-1,4-naphthoquinone: Characterization of 5-(Hydroperoxymethyl)-2‘-deoxycytidine and Stable Methyl Group Oxidation ProductsJournal of the American Chemical Society, 1996
- New Model for Calculation of Solvation Free Energies: Correction of Self-Consistent Reaction Field Continuum Dielectric Theory for Short-Range Hydrogen-Bonding EffectsThe Journal of Physical Chemistry, 1996
- Oxidation of Thymine to 5-Formyluracil in DNA: Mechanisms of Formation, Structural Implications, and Base Excision by Human Cell Free ExtractsBiochemistry, 1995
- Quantitative Determination of 8-Hydroxyguanine and Guanine by Isotope Dilution Mass SpectrometryAnalytical Biochemistry, 1995
- Accurate First Principles Calculation of Molecular Charge Distributions and Solvation Energies from Ab Initio Quantum Mechanics and Continuum Dielectric TheoryJournal of the American Chemical Society, 1994
- New pseudospectral algorithms for electronic structure calculations: Length scale separation and analytical two-electron integral correctionsThe Journal of Chemical Physics, 1994
- NMR structural studies of the ionizing radiation adduct 7-hydro-8-oxodeoxyguanosine (8-oxo-7H-dG) opposite deoxyadenosine in a DNA duplex. 8-Oxo-7H-dG(syn).cntdot.dA(anti) alignment at lesion siteBiochemistry, 1991
- Density-functional exchange-energy approximation with correct asymptotic behaviorPhysical Review A, 1988
- The use of capillary gas chromatography—mass spectrometry for identification of radiation-induced DNA base damage and DNA base—amino acid cross-linksJournal of Chromatography A, 1984
- Conformational analysis of the sugar ring in nucleosides and nucleotides. Improved method for the interpretation of proton magnetic resonance coupling constantsJournal of the American Chemical Society, 1973