Journal
THEORETICAL CHEMISTRY ACCOUNTS
Volume 120, Issue 4-6, Pages 429-435Publisher
SPRINGER
DOI: 10.1007/s00214-008-0418-7
Keywords
cytosine; hydrolytic deamination; B3LYP; mutation; DNA
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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 Delta G(not equal) = 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 (E-a = 117 +/- 4 kJ/mol).
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