Synthesis of cationic glucosamino nucleic acids for stabilizing oligonucleotides

Yoshiaki Kitamura; Shuichi Moribe; Yukio Kitade

doi:10.1016/j.bmcl.2018.08.024

Synthesis of cationic glucosamino nucleic acids for stabilizing oligonucleotides

Bioorg Med Chem Lett. 2018 Oct 15;28(19):3174-3176. doi: 10.1016/j.bmcl.2018.08.024. Epub 2018 Aug 25.

Authors

Yoshiaki Kitamura¹, Shuichi Moribe², Yukio Kitade³

Affiliations

¹ Department of Biomolecular Science, Graduate School of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan; Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan. Electronic address: kitamura@gifu-u.ac.jp.
² Department of Biomolecular Science, Graduate School of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.
³ Department of Biomolecular Science, Graduate School of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan; Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan; Department of Applied Chemistry, Faculty of Engineering, Aichi Institute of Technology, 1247 Yachigusa, Yakusa-cho, Toyota, Aichi 470-0392, Japan. Electronic address: ykkitade@aitech.ac.jp.

PMID: 30170941
DOI: 10.1016/j.bmcl.2018.08.024

Abstract

Glucosamino nucleic acids (GANAs) bearing a β-N-glycoside bond between carbon 1 of the glucosamine and the nucleobase nitrogen were synthesized and incorporated into oligonucleotides (4',6'-GANA and 3',6'-GANA). The thermal stability of oligonucleotide duplexes containing the GANA zwitterionic nucleotides was also investigated.

Keywords: Glucosamine; Nucleic acids; Oligonucleotides; Pyranosyl nucleosides; Zwitterionic nucleotides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Base Pairing
Biochemical Phenomena
Cations
Glucosamine / chemistry*
Hot Temperature
Nucleic Acid Hybridization
Nucleic Acids / chemical synthesis*
Nucleic Acids / chemistry
Oligonucleotides / chemistry*

Substances

Cations
Nucleic Acids
Oligonucleotides
Glucosamine