Ab initio molecular orbital study of the mispairing ability of a nucleotide base analogue, N4-aminocytosine.
The intrinsic properties of N4-aminocytosine, a base analogue of cytosine, are analyzed by an ab initio molecular orbital method. Relative stabilities of four possible isomeric structures of N4-aminocytosine are shown. The more stable isomer has the smaller dipole moment, so the relative stabilities of the isomers in solutions are subject to solvent polarity. The mutagenicity of this base analogue must arise because it can behave like either cytosine or thymine. It can form a guanine-cytosine-like base pair more easily than cytosine, and an adenine-thymine-like base pair less easily than thymine.
Aida
M
M
Biophysics Division, National Cancer Center Research Institute, Tokyo, Japan.
Negishi
K
K
Hayatsu
H
H
Maeda
M
M
D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003596:Cytosine / Q000031:analogs & derivatives*; D006860:Hydrogen Bonding; D007536:Isomerism; D009153:Mutagens; D013329:Structure-Activity Relationship
D009153:Mutagens; C025320:N(4)-aminocytosine; D003596:Cytosine