An ab initio molecular orbital study on the characteristics of 8-hydroxyguanine.
To investigate the mechanism by which the 8-hydroxyguanine residue in DNA affects the fidelity of DNA replication, the intrinsic properties of this modified base were investigated using an ab initio molecular orbital method. The most stable 8-hydroxyguanine form was revealed to be 6,8-diketo. The addition of an oxygen atom to the 8 position of a guanine base was shown to change the electrostatic potential of the molecule entirely and to give it a negative character. This effect may influence the local structure of 8-hydroxyguanine-containing DNA and the interaction with DNA polymerase, thereby resulting in infidelity of DNA replication.
Aida
M
M
Biophysics Division, National Cancer Center Research Institute, Tokyo, Japan.
Nishimura
S
S
D001482:Base Composition; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004249:DNA Damage; D004261:DNA Replication; D006147:Guanine / Q000031:analogs & derivatives*; D008958:Models, Molecular; D008968:Molecular Conformation; D012984:Software; D013698:Templates, Genetic
C024829:8-hydroxyguanine; D006147:Guanine