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Issue 47, 2015
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Synthesis and properties of 2′-O,4′-C-spirocyclopropylene bridged nucleic acid (scpBNA), an analogue of 2′,4′-BNA/LNA bearing a cyclopropane ring

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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.

Graphical abstract: Synthesis and properties of 2′-O,4′-C-spirocyclopropylene bridged nucleic acid (scpBNA), an analogue of 2′,4′-BNA/LNA bearing a cyclopropane ring

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Publication details

The article was received on 10 Mar 2015, accepted on 14 May 2015 and first published on 14 May 2015


Article type: Communication
DOI: 10.1039/C5CC02024G
Chem. Commun., 2015,51, 9737-9740

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

    T. Yamaguchi, M. Horiba and S. Obika, Chem. Commun., 2015, 51, 9737
    DOI: 10.1039/C5CC02024G

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