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Proton catalyzed hydrolytic deamination of cytosine: a computational study
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2008 (English)In: Theoretical Chemistry accounts, ISSN 1432-881X, E-ISSN 1432-2234, Vol. 120, no 4-6, p. 429-435Article in journal (Refereed) Published
Abstract [en]

Two pathways involving proton catalyzed hydrolytic deamination of cytosine (to uracil) are investigated at the PCM-corrected B3LYP/6-311G(d,p) level of theory, in the presence of an additional catalyzing water molecule. It is concluded that the pathway involving initial protonation at nitrogen in position 3 of the ring, followed by water addition at C4 and proton transfer to the amino group, is a likely route to hydrolytic deamination. The rate determining step is the addition of water to the cytosine, with a calculated free energy barrier in aqueous solution of G==140 kJ/mol. The current mechanism provides a lower barrier to deamination than previous work based on OH− catalyzed reactions, and lies closer to the experimental barrier derived from rate constants (Ea = 117 ± 4kJ/mol).

Place, publisher, year, edition, pages
Berlin Heidelberg: Springer , 2008. Vol. 120, no 4-6, p. 429-435
Keywords [en]
Cytosine · Hydrolytic deamination · B3LYP ·Mutation · DNA
National Category
Natural Sciences Theoretical Chemistry Chemical Sciences
Research subject
Chemistry
Identifiers
URN: urn:nbn:se:oru:diva-4656DOI: 10.1007/s00214-008-0418-7OAI: oai:DiVA.org:oru-4656DiVA, id: diva2:138955
Available from: 2008-10-24 Created: 2008-10-24 Last updated: 2017-12-14Bibliographically approved

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Eriksson, Leif A.

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