title: Synthesis and Properties of the 5-Methyluridine Derivative of 3,4-Dihydro-2H-pyran-Bridged Nucleic Acid (DpNA).
abstract: A novel 2'-O,4'-C-bridged nucleic acid, 3,4-dihydro-2H-pyran bridge moiety (DpNA), with a dioxabicyclo[3.2.1]oct-3-ene ring was designed. Construction of the dihydropyran bridge was achieved by dehydration of a six-membered hemiacetal ring, and the DpNA monomer was synthesized in 10 steps from 5-methyluridine (total yield 9%). The synthesized DpNA monomer was incorporated into oligonucleotides to examine the properties of the modified oligonucleotides. The DpNA-modified oligonucleotides possessed high affinity toward ssRNA and were more resistant to nucleases compared to the corresponding natural oligonucleotide.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University , 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.|Core Research for Evolutional Science and Technology (CREST), Japan Sciences and Technology Agency (JST) , 7 Gobancho, Chiyoda-ku, Tokyo 102-0076, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Osawa
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University , 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.|Faculty of Pharmaceutical Sciences, Tokushima Bunri University , Nishihama, Yamashiro-cho, Tokushima 770-8514, Japan.
authors.forename: Yoshiyuki
authors.initials: Y
authors.lastname: Hari
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University , 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
authors.forename: Masakazu
authors.initials: M
authors.lastname: Dohi
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University , 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
authors.forename: Yuya
authors.initials: Y
authors.lastname: Matsuda
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University , 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.|Core Research for Evolutional Science and Technology (CREST), Japan Sciences and Technology Agency (JST) , 7 Gobancho, Chiyoda-ku, Tokyo 102-0076, Japan.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Obika
mesh_terms: D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009690:Nucleic Acid Conformation; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D016376:Oligonucleotides, Antisense / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*; D012313:RNA / Q000737:chemistry*; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D001952:Bridged-Ring Compounds; D009841:Oligonucleotides; D016376:Oligonucleotides, Antisense; D011714:Pyrans; C009182:ribothymidine; D012313:RNA; D014529:Uridine