title: Efficient cross-linking to cytidine by functional nucleobases capable of in situ activation.
abstract: We have previously demonstrated that the ODNs with 2-amino-6-(2-phenylsulfoxyethyl)purine nucleoside derivative were capable of efficient interstrand cross-linking with cytidine selectively. In this new strategy, less reactive precursor was auto-activated within a duplex to generate 2-amino-6-vinylpurine derivative. However, it turned out that 2-amino-6-(2-phenylsulfinyl)-ethylpurine nucleoside was not applicable as the precursor for the synthesis of DNA oligomers with G-rich sequences. In this report, 2-amino-6-(2-methylsulfinylethyl)purine nucleoside has been proven to be more suitable as a precursor for DNA synthesis. In addition, the ODNs incorporating either 2-amino-6-(2-phenylsulfoxy ethyl)purine or 2-amino-6-vinylpurine showed high reactivity toward the cytidine at the target site but quite less reactivity was observed for it at non-target site, demonstrating high site-selectivity.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan.
authors.forename: T
authors.initials: T
authors.lastname: Kawasaki
authors.forename: F
authors.initials: F
authors.lastname: Nagatsugi
authors.forename: D
authors.initials: D
authors.lastname: Usui
authors.forename: M
authors.initials: M
authors.lastname: Maeda
authors.forename: S
authors.initials: S
authors.lastname: Sasaki
mesh_terms: D001483:Base Sequence; D003432:Cross-Linking Reagents; D003562:Cytidine / Q000737:chemistry*; D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D011684:Purine Nucleosides; D013454:Sulfoxides
chemical_list: D003432:Cross-Linking Reagents; D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides; D011684:Purine Nucleosides; D013454:Sulfoxides; D003562:Cytidine; D004247:DNA