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Synthesis and properties of 2'-O,4'-C-spirocycl opropylene bridged nucleic acid (scpBNA), an analogue of 2',4'-BNA/LNA bearing a cyclopropane ring

2'-O,4'-C-Spirocyclopr opylene 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 excel... Full description

Journal Title: Chemical Communications: Chem Comm May 2015, Vol.51(47), pp.9737-9740
Main Author: Yamaguchi, Takao
Other Authors: Horiba, Masahiko , Obika, Satoshi
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 1359-7345 ; E-ISSN: 1364-548X ; DOI: 10.1039/c5cc02024g
Link: http://search.proquest.com/docview/1701116214/?pq-origsite=primo
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title: Synthesis and properties of 2'-O,4'-C-spirocycl opropylene bridged nucleic acid (scpBNA), an analogue of 2',4'-BNA/LNA bearing a cyclopropane ring
format: Article
creator:
  • Yamaguchi, Takao
  • Horiba, Masahiko
  • Obika, Satoshi
subjects:
  • Genes
  • Cyclopropane
  • Ribonucleic Acids
  • Analogue
  • Bearing
  • Synthesis
  • Stability
  • Oligonucleotides
  • Nucleic Acids
  • Miscellaneous Sciences (So)
  • Chemical and Electrochemical Properties (MD)
  • Chemical and Electrochemical Properties (Ep)
  • Chemical and Electrochemical Properties (Ed)
  • Chemical and Electrochemical Properties (EC)
ispartof: Chemical Communications: Chem Comm, May 2015, Vol.51(47), pp.9737-9740
description: 2'-O,4'-C-Spirocyclopr opylene 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.
language: eng
source:
identifier: ISSN: 1359-7345 ; E-ISSN: 1364-548X ; DOI: 10.1039/c5cc02024g
fulltext: fulltext
issn:
  • 13597345
  • 1359-7345
  • 1364548X
  • 1364-548X
url: Link


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titleSynthesis and properties of 2'-O,4'-C-spirocycl opropylene bridged nucleic acid (scpBNA), an analogue of 2',4'-BNA/LNA bearing a cyclopropane ring
creatorYamaguchi, Takao ; Horiba, Masahiko ; Obika, Satoshi
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ispartofChemical Communications: Chem Comm, May 2015, Vol.51(47), pp.9737-9740
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subjectGenes ; Cyclopropane ; Ribonucleic Acids ; Analogue ; Bearing ; Synthesis ; Stability ; Oligonucleotides ; Nucleic Acids ; Miscellaneous Sciences (So) ; Chemical and Electrochemical Properties (MD) ; Chemical and Electrochemical Properties (Ep) ; Chemical and Electrochemical Properties (Ed) ; Chemical and Electrochemical Properties (EC)
description2'-O,4'-C-Spirocyclopr opylene 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.
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titleSynthesis and properties of 2'-O,4'-C-spirocycl opropylene bridged nucleic acid (scpBNA), an analogue of 2',4'-BNA/LNA bearing a cyclopropane ring
description2'-O,4'-C-Spirocyclopr opylene 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.
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titleSynthesis and properties of 2'-O,4'-C-spirocycl opropylene bridged nucleic acid (scpBNA), an analogue of 2',4'-BNA/LNA bearing a cyclopropane ring
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atitleSynthesis and properties of 2'-O,4'-C-spirocycl opropylene bridged nucleic acid (scpBNA), an analogue of 2',4'-BNA/LNA bearing a cyclopropane ring
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abstract2'-O,4'-C-Spirocyclopr opylene 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.
doi10.1039/c5cc02024g
urlhttp://search.proquest.com/docview/1701116214/
date2015-05-01