Theoretical Chemistry Accounts

, Volume 122, Issue 3, pp 179–188

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

Authors

  • Adam Moser
    • Department of ChemistryUniversity of Minnesota
  • Rebecca Guza
    • Department of Medicinal Chemistry and the Cancer CenterUniversity of Minnesota
  • Natalia Tretyakova
    • Department of Medicinal Chemistry and the Cancer CenterUniversity of Minnesota
    • Department of ChemistryUniversity of Minnesota
Regular Article

DOI: 10.1007/s00214-008-0497-5

Cite this article as:
Moser, A., Guza, R., Tretyakova, N. et al. Theor Chem Account (2009) 122: 179. doi:10.1007/s00214-008-0497-5

Abstract

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.

Copyright information

© Springer-Verlag 2008