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Effects of OH radical addition on proton transfer in the guanine-cytosine base pair
Örebro University, Department of Natural Sciences. (Biophysical Chemistry)
2007 (English)In: Journal of Physical Chemistry B, ISSN 1520-6106, E-ISSN 1520-5207, Vol. 111, no 23, p. 6571-6576Article in journal (Refereed) Published
Abstract [en]

Double proton transfer (PT) reactions in guanine-cytosine OH radical adducts are studied by the hybrid density functional B3LYP approach. Concerted and stepwise proton-transfer processes are explored between N1(H) on guanine (G) and N3 on cytosine (C), and between N4(H) on C and O6 on G. All systems except GC6OH display a concerted mechanism. 8OHGC has the highest dissociation energy and is 1.2 kcal/mol more stable than the nonradical GC base pair. The origin of the interactions are investigated through the estimation of intrinsic acid-basic properties of the *OH-X monomer (X = G or C). Solvent effects play a significant role in reducing the dissociation energy. The reactions including *OH-C adducts have significantly lower PT barriers than both the nonradical GC pair and the *OH-G adducts. All reactions are endothermic, with the GC6OH --> GC6OHPT reaction has the lowest reaction energy (4.6 kcal/mol). In accordance with earlier results, the estimated NBO charges show that the G moiety carries a slight negative charge (and C a corresponding positive one) in each adduct. The formation of a partial ion pair may be a potential factor leading to the PT reactions being thermodynamically unfavored.

Place, publisher, year, edition, pages
Washington, DC: American Chemical Society , 2007. Vol. 111, no 23, p. 6571-6576
Keywords [en]
Base Pairing, Cytosine, Guanine, Hydroxyl Radical, Molecular Structure, Nucleic Acids, Computational chemistry
National Category
Theoretical Chemistry Natural Sciences Chemical Sciences
Research subject
Chemistry
Identifiers
URN: urn:nbn:se:oru:diva-4107DOI: 10.1021/jp071772lPubMedID: 17506547OAI: oai:DiVA.org:oru-4107DiVA, id: diva2:138406
Available from: 2007-11-02 Created: 2007-11-02 Last updated: 2017-12-14Bibliographically approved

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Eriksson, Leif A.

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