TY - JOUR
T1 - Size-expanded DNA bases
T2 - An ab initio study of their structural and electronic properties
AU - Fuentes-Cabrera, Miguel
AU - Sumpter, Bobby G.
AU - Wells, Jack C.
PY - 2005/11/10
Y1 - 2005/11/10
N2 - The size-expanded DNA bases, xA, xC, xG, and xT, are benzo-homologue forms of the natural DNA bases; i.e., their structure can be seen as the fusion of a natural base and a benzene ring. Recently, a variety of DNAs, known as xDNAs, have been synthesized in which size-expanded and natural bases are paired. In this paper we use second-order Møller-Plesset perturbation theory and density functional theory to investigate the structural and electronic properties of xA, xC, xG, and xT and their natural counterparts. We find that whereas natural and size-expanded bases have both nonplanar amino groups the latter have also nonplanar aromatic rings. When density functional theory is used to investigate the electronic properties of size-expanded and natural bases, it is found that the HOMO-LUMO gap of the size-expanded bases is smaller than that of the natural bases. Also, xG should be easier to oxidize than G.
AB - The size-expanded DNA bases, xA, xC, xG, and xT, are benzo-homologue forms of the natural DNA bases; i.e., their structure can be seen as the fusion of a natural base and a benzene ring. Recently, a variety of DNAs, known as xDNAs, have been synthesized in which size-expanded and natural bases are paired. In this paper we use second-order Møller-Plesset perturbation theory and density functional theory to investigate the structural and electronic properties of xA, xC, xG, and xT and their natural counterparts. We find that whereas natural and size-expanded bases have both nonplanar amino groups the latter have also nonplanar aromatic rings. When density functional theory is used to investigate the electronic properties of size-expanded and natural bases, it is found that the HOMO-LUMO gap of the size-expanded bases is smaller than that of the natural bases. Also, xG should be easier to oxidize than G.
UR - http://www.scopus.com/inward/record.url?scp=28144442040&partnerID=8YFLogxK
U2 - 10.1021/jp055210i
DO - 10.1021/jp055210i
M3 - Article
C2 - 16853737
AN - SCOPUS:28144442040
SN - 1520-6106
VL - 109
SP - 21135
EP - 21139
JO - Journal of Physical Chemistry B
JF - Journal of Physical Chemistry B
IS - 44
ER -