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Issue 35, 2018
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Facile synthesis and fundamental properties of an N-methylguanidine-bridged nucleic acid (GuNA[NMe])

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Abstract

An N-methylguanidine-bridged nucleic acid (GuNA[NMe]), a guanidine-bridged nucleic acid (GuNA) bearing a methyl substituent at the bridge, was successfully synthesised and incorporated into oligonucleotides. By employing an acetyl protecting group, GuNA[NMe]-modified oligonucleotides bearing acid-sensitive purine nucleobases were successfully prepared. The obtained GuNA[NMe]-modified oligonucleotides exhibit excellent binding affinity towards the complementary single-stranded RNA and DNA. Furthermore, even a single GuNA[NMe] modification provides robust enzymatic stability, similar to that achieved by the well-established phosphorothioate backbone modification. These data indicate that such a GuNA[NMe] represents a valuable modification for the development of therapeutic oligonucleotides.

Graphical abstract: Facile synthesis and fundamental properties of an N-methylguanidine-bridged nucleic acid (GuNA[NMe])

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Publication details

The article was received on 02 Jun 2018, accepted on 27 Jun 2018 and first published on 30 Aug 2018


Article type: Paper
DOI: 10.1039/C8OB01307A
Citation: Org. Biomol. Chem., 2018,16, 6531-6536
  • Open access: Creative Commons BY-NC license
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    Facile synthesis and fundamental properties of an N-methylguanidine-bridged nucleic acid (GuNA[NMe])

    N. Horie, S. Kumagai, Y. Kotobuki, T. Yamaguchi and S. Obika, Org. Biomol. Chem., 2018, 16, 6531
    DOI: 10.1039/C8OB01307A

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