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- Title
Effects of electron attachment on C<sub>5′</sub>&bond;O<sub>5′</sub> and C<sub>1′</sub>&bond;N<sub>1</sub> bond cleavages of pyrimidine nucleotides: A theoretical study.
- Authors
Hujun Xie; Ruibo Wu; Fei Xia; Zexing Cao
- Abstract
Sugar-base C1′&bond;N1 and phosphate-sugar C5′&bond;O5′ bond breakings of 2′-deoxycytidine-5′-monophosphates (dCMP) and 2′-deoxythymidine-5′- monophosphates (dTMP) and their radical anions have been explored theoretically at the B3LYP/DZP++ level of theory. Calculations show that the low-energy electrons attachment to the pyrimidine nucleotides results in remarkable structural and chemical bonding changes. Predicted Gibbs free energies of reaction ΔG for the C5′&bond;O5′ bond dissociation process of the radical anions are -14.6 and -11.5 kcal mol-1, respectively, and such dissociation processes may be intrinsically spontaneous in the gas phase. Furthermore, the C5′&bond;O5′ bond cleavage processes of the anionic dCMP and dTMP were predicted to have activation energies of 6.9 and 8.0 kcal mol-1 in the gas phase, respectively, much lower than the barriers for the C1′&bond;N1 bond breaking process, showing that the C&bond;O bond dissociation in DNA single strand breaks is a dominant process as observed experimentally. © 2008 Wiley Periodicals, Inc. J Comput Chem 2008
- Subjects
ELECTRONS; GLYCOSIDES; DENSITY functionals; FUNCTIONAL analysis; DNA; NUCLEIC acids
- Publication
Journal of Computational Chemistry, 2008, Vol 29, Issue 12, p2025
- ISSN
0192-8651
- Publication type
Article
- DOI
10.1002/jcc.20967