title: Triazolyl donor/acceptor chromophore decorated unnatural nucleosides and oligonucleotides with duplex stability comparable to that of a natural adenine/thymine pair.
abstract: We report the design and synthesis of triazolyl donor/acceptor unnatural nucleosides via click chemistry and studies on the duplex stabilization of DNA containing two such new nucleosides. The observed duplex stabilization among the self-pair/heteropair has been found to be comparable to that of a natural A/T pair. Our observations on the comparable duplex stabilization has been explained on the basis of possible π-π stacking and/or charge transfer interactions between the pairing partners. The evidence of ground-state charge transfer complexation came from the UV-vis spectra and the static quenching of fluorescence in a heteropair. We have also exploited one of our unnatural DNAs in stabilizing abasic DNA.
authors.affiliation: Bio-organic Chemistry Laboratory, Department of Chemistry, Indian Institute of Technology, Guwahati-781039, India. ssbag75@iitg.ernet.in
authors.forename: Subhendu Sekhar
authors.initials: SS
authors.lastname: Bag
authors.forename: Sangita
authors.initials: S
authors.lastname: Talukdar
authors.forename: Katsuhiko
authors.initials: K
authors.lastname: Matsumoto
authors.forename: Rajen
authors.initials: R
authors.lastname: Kundu
mesh_terms: D000225:Adenine; D020029:Base Pairing; D057930:Click Chemistry; D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D005453:Fluorescence; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D013941:Thymine / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009705:Nucleosides; D009841:Oligonucleotides; D014230:Triazoles; D004247:DNA; D000225:Adenine; D013941:Thymine