title: 2',4'-BNA derivatives bearing an unnatural nucleobase: synthesis and application to triplex-forming oligonucleotides.
abstract: Recognition of dsDNA by a triplex-forming oligonucleotide (TFO) is limited to homopurine x homopyrimidine sequences. Therefore, it is necessary to develop novel nucleoside analogues which recognize pyrimidine x purine basepairs (C x G or T x A). We have designed and synthesized novel 2',4'-BNA/LNA monomers bearing 3-hydroxybenzene and indole as a nucleobase (3HB(B) and In(B)), and these nucleoside analogues have been introduced into TFOs. On melting temperature (Tm) measurements, 3HB(B) and In(B) were found to interact with T x A base pair interruption with moderate binding affinity.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
authors.forename: Hiroyasu
authors.initials: H
authors.lastname: Inohara
authors.forename: Satoshi
authors.initials: S
authors.lastname: Obika
authors.forename: Takeshi
authors.initials: T
authors.lastname: Imanishi
mesh_terms: D001483:Base Sequence; D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry* / Q000235:genetics; D006860:Hydrogen Bonding; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D008969:Molecular Sequence Data; D009690:Nucleic Acid Conformation; D009841:Oligonucleotides / Q000737:chemistry*; D019800:Phenol / Q000138:chemical synthesis / Q000737:chemistry*; D044366:Transition Temperature
chemical_list: D007211:Indoles; D009841:Oligonucleotides; C051802:triplex DNA; D019800:Phenol; C030374:indole; D004247:DNA