Evaluation of base recognition abilities of 2'-deoxynucleoside N-oxide derivatives by polymerase reactions.
The main products obtained by oxidation of cytosine and adenine bases with hydrogen peroxide are cytosine and adenine N-oxide derivatives. There is a possibility that these N-oxide derivatives are mutagenic in genomic DNA like 8-oxoguanine or thymine glycol. Although the chemical synthesis and properties of 2'-deoxynucleoside N-oxide derivatives have been well established, little has been reported about the chemical and biochemical behavior of oligodeoxynucleotides (ODNs) containing these modified 2'-deoxynucleoside. In this study, we examined their base recognition ability by DNA polymerase reactions. It was found that these modified derivatives were incorporated into the 3'-terminal site of an ODN by DNA polymerase selecting accurately the complementary G or T base on a template ODN. In the incorporation reaction using template ODNs containing 2'-deoxynucleoside N-oxide bases, their N-oxide bases were selectively recognized by the complementary 5'-triphosphate (dGTP or dTTP).
Tsunoda
Hirosuke
H
Department of Life Science, Tokyo Institute of Technology, Yokohama 226-8501, Japan.
Ohkubo
Akihiro
A
Seio
Kohji
K
Sekine
Mitsuo
M
D000225:Adenine / Q000031:analogs & derivatives* / Q000737:chemistry; D020029:Base Pairing; D003497:Cyclic N-Oxides / Q000737:chemistry*; D004259:DNA-Directed DNA Polymerase / Q000378:metabolism*; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000737:chemistry; D009838:Oligodeoxyribonucleotides / Q000096:biosynthesis / Q000737:chemistry; D013379:Substrate Specificity; D013698:Templates, Genetic
D003497:Cyclic N-Oxides; D009838:Oligodeoxyribonucleotides; D003841:Deoxycytidine; C030755:adenine-N-oxide; D004259:DNA-Directed DNA Polymerase; D000225:Adenine