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Mechanism of nitric oxide induced deamination of cytosine
Vise andre og tillknytning
2009 (engelsk)Inngår i: Physical Chemistry, Chemical Physics - PCCP, ISSN 1463-9076, E-ISSN 1463-9084, Vol. 11, nr 14, s. 2379-2386Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
2009. Vol. 11, nr 14, s. 2379-2386
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URN: urn:nbn:se:oru:diva-13351DOI: 10.1039/b818669cISI: 000264640100004OAI: oai:DiVA.org:oru-13351DiVA, id: diva2:387545
Tilgjengelig fra: 2011-01-14 Laget: 2011-01-11 Sist oppdatert: 2017-12-11bibliografisk kontrollert

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