Density functional study of the influence of C5 cytosine substitution in base pairs with guanine

Adam Moser, Rebecca Guza, Natalia Tretyakova, Darrin M. York

Research output: Contribution to journalArticle

22 Scopus citations


The present study employs density-functional electronic structure methods to investigate the effect of chemical modification at the C5 position of cytosine. A series of experimentally motivated chemical modifications are considered, including alkyl, halogen, aromatic, fused ring, and strong σ and π withdrawing functional groups. The effect of these modifications on cytosine geometry, electronic structure, proton affinities, gas phase basicities, cytosine-guanine base pair hydrogen bond network and corresponding nucleophilicity at guanine are examined. Ultimately, these results play a part in dissecting the effect of endogenous cytosine methylation on the reactivity of neighboring guanine toward carcinogens and DNA alkylating agents.

Original languageEnglish (US)
Pages (from-to)179-188
Number of pages10
JournalTheoretical Chemistry Accounts
Issue number3-4
Publication statusPublished - Mar 1 2009
Externally publishedYes


All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry

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