title: Triplex-forming ability of oligonucleotides containing 1-aryl-1,2,3-triazole nucleobases linked via a two atom-length spacer.
abstract: Phosphoramidites containing 2-propynyloxy or 1-butyn-4-yl as nucleobase precursors were synthesized and introduced into oligonucleotides using an automated DNA synthesizer. Copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition of the oligonucleotides with various azides gave the corresponding triazolylated oligonucleotides, triplex-forming ability of these synthetic oligonucleotides with double-stranded DNA targets was evaluated by UV melting experiments. It was found that nucleobases containing 2-(1-m-carbonylaminophenyl-1,2,3-triazol-4-yl)ethyl units likely interacted with A of a TA base pair in a parallel triplex DNA.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan. hari@phs.osaka-u.ac.jp
authors.forename: Yoshiyuki
authors.initials: Y
authors.lastname: Hari
authors.forename: Motoi
authors.initials: M
authors.lastname: Nakahara
authors.forename: Satoshi
authors.initials: S
authors.lastname: Obika
mesh_terms: D020029:Base Pairing; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D061565:Cycloaddition Reaction; D004247:DNA / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D044367:Phase Transition; D044366:Transition Temperature; D014230:Triazoles / Q000737:chemistry*; D014466:Ultraviolet Rays
chemical_list: D009705:Nucleosides; D009841:Oligonucleotides; D014230:Triazoles; C051802:triplex DNA; D003300:Copper; D004247:DNA
keywords: 1,3-Dipolar cycloaddition; Artificial nucleobases; Triazoles; Triplex DNA; Triplex-forming oligonucleotides