title: Synthesis and properties of DNA oligomers containing 2'-deoxycytidine-N-oxide.
abstract: The main product obtained by oxidation of 2'-deoxycytidine with hydrogen peroxide is 2'-deoxycytidine N-oxide. Although its chemical synthesis and properties of 2'-deoxycytidine N-oxide have been well established, little has been reported about the chemical and biochemical behavior of DNA oligomers containing this modified deoxynucleoside. In this study, we synthesized DNA oligomers containing 2'-deoxycytidine N-oxide by use of a post-synthetic oxidative method. It should be noted that this modified base could be incorporated in oligodeoxynucleotides at appropriate positions by this strategy. The ability of the base pair formation was significantly low because of the blocking of the canonical hydrogen bonding site.
authors.affiliation: Department of Life Science, Tokyo institute of Technology, 4259 Nagatsuta, Midoriku, Yokohama, 226-8501, Japan.
authors.forename: Hirosuke
authors.initials: H
authors.lastname: Tsunoda
authors.forename: Akihiro
authors.initials: A
authors.lastname: Ohkubo
authors.forename: Haruhiko
authors.initials: H
authors.lastname: Taguchi
authors.forename: Kohji
authors.initials: K
authors.lastname: Seio
authors.forename: Mitsuo
authors.initials: M
authors.lastname: Sekine
mesh_terms: D020029:Base Pairing; D003497:Cyclic N-Oxides / Q000737:chemistry*; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000737:chemistry; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction
chemical_list: C522091:2'-deoxycytidine-N-oxide; D003497:Cyclic N-Oxides; D009838:Oligodeoxyribonucleotides; D003841:Deoxycytidine