Chitotriazolan (poly(β(1-4)-2-(1H-1,2,3-triazol-1-yl)-2-deoxy-D-glucose)) derivatives: Synthesis, characterization, and evaluation of antibacterial activity

Sankar Rathinam, Martha Ásdís Hjálmarsdóttir, Mikkel B. Thygesen, Már Másson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Here we describe the first synthesis of a new type of polysaccharides derived from chitosan. In these structures, the 2-amino group on the pyranose ring was quantitively replaced by an aromatic 1,2,3-triazole moiety. The 2-amino group of chitosan and di-TBDMS chitosan was converted into an azide by diazo transfer reaction. The chitosan azide and TBDMS-chitosan azide were poorly soluble but could be fully converted to triazoles by “copper-catalysed Huisgen cycloaddition” in DMF or DMSO. The reaction could be done with different alkynes but derivatives lacking cationic or anionic groups were poorly soluble or insoluble in tested aqueous and organic solvents. Derivatives with N,N-dimethylaminomethyl, N,N,N-trimethylammoniummethyl, sulfonmethyl, and phosphomethyl groups linked to the 4-position of the triazole moiety were soluble in water at neutral or basic conditions and could be analyzed by 1H, 13C APT, COSY, and HSQC NMR. The quaternized cationic chitotriazolan's had high activity against S. aureus and E. coli, whereas the anionic chitotriazolan's lacked activity.

Original languageEnglish
Article number118162
Pages (from-to)118162
Number of pages118162
JournalCarbohydrate Polymers
Volume267
DOIs
Publication statusPublished - 1 Sep 2021

Bibliographical note

Copyright © 2021 Elsevier Ltd. All rights reserved.

The research work was funded by the Icelandic Research Fund (Rannis Grant No. 1709-0210) and by a doctoral grant from the University of Iceland research fund. We thank Primex ehf for donating the chitosan starting material. We thank Dr. Sigríður Jónsdóttir for running the 1H NMR samples and Dr. Svetlana Solodova for the SEC-MALLS analysis.

Other keywords

  • Anti-Bacterial Agents/chemical synthesis
  • Carbohydrate Sequence
  • Escherichia coli/drug effects
  • Glucans/chemical synthesis
  • Microbial Sensitivity Tests
  • Solubility
  • Staphylococcus aureus/drug effects
  • Triazoles/chemical synthesis
  • Water/chemistry
  • Materials Chemistry
  • Polymers and Plastics
  • Organic Chemistry
  • click chemistry
  • Antimicrobial
  • Chitosan
  • Lífræn efnafræði

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