title: Synthesis and properties of 2'-O,4'-C-spirocyclopropylene bridged nucleic acid (scpBNA), an analogue of 2',4'-BNA/LNA bearing a cyclopropane ring.
abstract: 2'-O,4'-C-Spirocyclopropylene bridged nucleic acid (scpBNA), an analogue of 2'-O,4'-C-methylene bridged nucleic acid (2',4'-BNA/LNA) bearing a cyclopropane ring at the 6'-position, was synthesized and successfully incorporated into oligonucleotides. The scpBNA-modified oligonucleotides showed excellent duplex-forming ability with complementary single-stranded RNA and exhibited increased enzymatic stability as compared to the corresponding natural and 2',4'-BNA/LNA-modified oligonucleotides. Our results demonstrate the potential of scpBNA for gene therapeutics, such as antisense technology.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan. obika@phs.osaka-u.ac.jp.
authors.forename: Takao
authors.initials: T
authors.lastname: Yamaguchi
authors.forename: Masahiko
authors.initials: M
authors.lastname: Horiba
authors.forename: Satoshi
authors.initials: S
authors.lastname: Obika
mesh_terms: D001952:Bridged-Ring Compounds / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D004277:DNA, Single-Stranded / Q000737:chemistry*; D005092:Exonucleases / Q000378:metabolism*; D009690:Nucleic Acid Conformation; D009841:Oligonucleotides / Q000737:chemistry*; D012313:RNA / Q000737:chemistry*
chemical_list: D001952:Bridged-Ring Compounds; D003521:Cyclopropanes; D004277:DNA, Single-Stranded; D009841:Oligonucleotides; C477371:locked nucleic acid; D012313:RNA; C030797:cyclopropane; D005092:Exonucleases; C022650:spleen exonuclease