title: Synthesis and evaluation of a novel 2',5'-bridged nucleic acid with sugar conformation fixed to S-type by N-O linkage.
abstract: Our work involves the design and synthesis of various types of bridged nucleic acid (BNA). Here, we describe a novel 2'-O, 5'-N-bridged nucleic acid, 2',5'-BNA(ON), whose sugar puckering is fixed to the S-type conformation by N-O linkage. A 2',5'-BNA(ON)-containing dimer unit was synthesized via a coupling reaction between a protected 2',5'-BNA(ON)-U monomer and a thymidine derivative. Introduction of 2',5'-BNA(ON)-U into DNA was carried out using conventional phosphoramidite chemistry with a DNA synthesizer. The hybridization abilities of 2',5'-BNA(ON)-U-modified oligonucleotides with their DNA or RNA complements were evaluated.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Kodama
authors.forename: Chieko
authors.initials: C
authors.lastname: Matsuo
authors.forename: Hidetsugu
authors.initials: H
authors.lastname: Ori
authors.forename: Satoshi
authors.initials: S
authors.lastname: Obika
authors.forename: Kazuyuki
authors.initials: K
authors.lastname: Miyashita
authors.forename: Takeshi
authors.initials: T
authors.lastname: Imanishi
mesh_terms: D001952:Bridged-Ring Compounds / Q000138:chemical synthesis / Q000737:chemistry; D002236:Carbohydrate Conformation; D009841:Oligonucleotides / Q000737:chemistry*
chemical_list: D001952:Bridged-Ring Compounds; D009841:Oligonucleotides