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

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-mod...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 51; no. 47; pp. 9737 - 9740
Main Authors Yamaguchi, Takao, Horiba, Masahiko, Obika, Satoshi
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2015
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
THERAPEUTICS
NUCLEOSIDE ANALOGS
RECOGNITION
5-METHYLCYTOSINE
MODIFIED OLIGONUCLEOTIDES
RNA SELECTIVE HYBRIDIZATION
RESISTANCE
ENA
ANTISENSE OLIGONUCLEOTIDES
LNA
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc02024g