Issue 35, 2018

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

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])

Supplementary files

Article information

Article type
Paper
Submitted
02 Jun 2018
Accepted
27 Jun 2018
First published
30 Aug 2018
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2018,16, 6531-6536

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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