Synthesis and properties of DNA oligomers containing 2'-deoxynucleoside N-oxide derivatives.
Cytosine and adenine N-oxide derivatives have long been known as products resulting from the oxidative damage of DNA by peroxides such as hydrogen peroxide. Although the synthesis and properties of 2'-deoxynucleoside N-oxide derivatives have been well described, little has been reported about the chemical and biochemical behavior of initially formed DNA oligomers containing these N-oxide bases. In this study, we established a convenient method for the solid-phase synthesis of oligodeoxynucleotides incorporating 2'-deoxycytidine N-oxide (dC O) or 2'-deoxyadenosine N-oxide (dA O) by using the postsynthetic oxidation of N-protected DNA oligomers except for the target dC or dA site with m-CPBA in MeOH in a highly selective manner. In this strategy, the benzoyl, phthaloyl, and (4-isopropylphenoxy)acetyl groups proved to serve as base protecting groups to avoid oxidation of adenine, cytosine, and guanine, respectively, at the unmodified sites.
Tsunoda
Hirosuke
H
Department of Life Science, Tokyo Institute of Technology, CREST, Japan Science and Technology Agency, Yokohama, 226-8501, Japan.
Ohkubo
Akihiro
A
Taguchi
Haruhiko
H
Seio
Kohji
K
Sekine
Mitsuo
M
D001704:Biopolymers / Q000737:chemistry*; D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D001704:Biopolymers; D009705:Nucleosides; D010087:Oxides; D004247:DNA