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The fate of H atom adducts to 3'-Uridine Monophosphate
Inst Chem Phys, Sch Sci, Beijing Inst Technol, Beijing, Peoples R China.
Inst Chem Phys, Sch Sci, Beijing Inst Technol, Beijing, Peoples R China.
Örebro University, School of Science and Technology. Sch Chem, Natl Univ Ireland, Galway, Ireland.
2010 (English)In: Journal of Physical Chemistry B, ISSN 1520-6106, E-ISSN 1520-5207, Vol. 114, no 29, p. 9617-9621Article in journal (Refereed) Published
Abstract [en]

The stabilities of the adducts deriving from H free radical addition to the O2, O4, and C5 positions of 3'-uridine monophosphate (3'UMP) are studied by the hybrid density functional B3LYP approach. Upon H atom addition at the O2 position, a concerted low-barrier proton-transfer process will initially occur, followed by the potential ruptures of the N-glycosidic or beta-phosphate bonds. The rupture barriers are strongly influenced by the rotational configuration of the phosphate group at the 3' terminal, and are influenced by bulk solvation effects. The O4-H adduct has the highest thermal stability, as the localization of the unpaired electron does not enable cleavage of either the C1'-N1 or the C3'-O(P) bonds. For the most stable adduct, with H atom added to the C5 position, the rate-controlled step is the H2'a abstraction by the C6 radical site, after which the subsequent strand rupture reactions proceed with low barriers. The main unpaired electron densities are presented for the transient species. Combined with previous results, it is concluded that the H atom adducts are more facile to drive the strand scission rather than N-glycosidic bond ruptures within the nucleic acid bases.

Place, publisher, year, edition, pages
2010. Vol. 114, no 29, p. 9617-9621
National Category
Chemical Sciences
Research subject
Chemistry
Identifiers
URN: urn:nbn:se:oru:diva-12908DOI: 10.1021/jp100116wISI: 000280071400034OAI: oai:DiVA.org:oru-12908DiVA, id: diva2:383328
Available from: 2011-01-04 Created: 2011-01-03 Last updated: 2018-04-23Bibliographically approved

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Eriksson, Leif A.

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