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Mechanism of nitric oxide induced deamination of cytosine
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2009 (English)In: Physical Chemistry, Chemical Physics - PCCP, ISSN 1463-9076, E-ISSN 1463-9084, Vol. 11, no 14, p. 2379-2386Article in journal (Refereed) Published
Abstract [en]

A five-step mechanism is proposed for the NO center dot-induced deamination of cytosine. It has been investigated using DFT calculations, including both explicit water molecules and a bulk solvent model to mimic an aqueous environment. According to this mechanism, cytosine first undergoes tautomerization with the assistance of a water molecule from the bulk. A NO+ cation produced by the autooxidation of NO center dot is subsequently added to the exocyclic imino group of the cytosine imine tautomer. The resulting adduct is able to undergo a tautomerization step with the participation of a water molecule to produce a cytosine in which a -N2OH group is attached to carbon C4. Protonation of the oxygen of the latter gives a water molecule which dissociates instantaneously, leading to a pyrimidinic diazonium cation. This constitutes the rate-determining step of the mechanism with an activation free energy of 92.6 kJ mol(-1). The last step, which is highly exergonic, represents the driving force of the reaction. It is the substitution of the -N-2(+) terminal group by a water molecule which simultaneously allows the transfer of one of the two hydrogens to the bulk. Thus, the two products of the reaction consist of a nitrogen molecule and the enol tautomer of uracil in equilibrium with the keto form.

Place, publisher, year, edition, pages
2009. Vol. 11, no 14, p. 2379-2386
National Category
Chemical Sciences
Research subject
Chemistry
Identifiers
URN: urn:nbn:se:oru:diva-13351DOI: 10.1039/b818669cISI: 000264640100004OAI: oai:DiVA.org:oru-13351DiVA, id: diva2:387545
Available from: 2011-01-14 Created: 2011-01-11 Last updated: 2017-12-11Bibliographically approved

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Eriksson, Leif A.

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