TY - JOUR
T1 - Density functional study of the influence of C5 cytosine substitution in base pairs with guanine
AU - Moser, Adam
AU - Guza, Rebecca
AU - Tretyakova, Natalia
AU - York, Darrin M.
PY - 2009/3/1
Y1 - 2009/3/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=60749093303&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=60749093303&partnerID=8YFLogxK
U2 - 10.1007/s00214-008-0497-5
DO - 10.1007/s00214-008-0497-5
M3 - Article
C2 - 19890472
AN - SCOPUS:60749093303
VL - 122
SP - 179
EP - 188
JO - Theoretical Chemistry Accounts
JF - Theoretical Chemistry Accounts
SN - 1432-881X
IS - 3-4
ER -