Effects of electron attachment on C5'-O5' and C1'-N1 bond cleavages of pyrimidine nucleotides : A theoretical study
(c) 2008 Wiley Periodicals, Inc.
| Veröffentlicht in: | Journal of computational chemistry. - 1984. - 29(2008), 12 vom: 15. Sept., Seite 2025-32 |
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| Weitere Verfasser: | , , |
| Format: | Online-Aufsatz |
| Sprache: | English |
| Veröffentlicht: |
2008
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| Zugriff auf das übergeordnete Werk: | Journal of computational chemistry |
| Schlagworte: | Journal Article Research Support, Non-U.S. Gov't Pyrimidine Nucleotides |
| Zusammenfassung: | (c) 2008 Wiley Periodicals, Inc. Sugar-base C(1')-N(1) and phosphate-sugar C(5')-O(5') 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 DeltaG for the C(5')-O(5') 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 C(5')-O(5') 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 C(1')-N(1) bond breaking process, showing that the C-O bond dissociation in DNA single strand breaks is a dominant process as observed experimentally |
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| Beschreibung: | Date Completed 11.09.2008 Date Revised 28.07.2008 published: Print Citation Status MEDLINE |
| ISSN: | 1096-987X |
| DOI: | 10.1002/jcc.20967 |