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
| Autor: | Martha Á. Hjálmarsdóttir, Mikkel B. Thygesen, Sankar Rathinam, Már Másson |
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| Rok vydání: | 2021 |
| Předmět: |
Staphylococcus aureus
1 2 3-Triazole Polymers and Plastics Triazole Microbial Sensitivity Tests 02 engineering and technology 010402 general chemistry 01 natural sciences Medicinal chemistry chemistry.chemical_compound Escherichia coli Materials Chemistry Moiety Glucans Organic Chemistry Cationic polymerization Water Triazoles 021001 nanoscience & nanotechnology Anti-Bacterial Agents 0104 chemical sciences Carbohydrate Sequence Solubility chemistry Pyranose Click chemistry Diazo Azide 0210 nano-technology |
| Zdroj: | Rathinam, S, Hjálmarsdóttir, M Á, Thygesen, M B & Másson, M 2021, ' 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 ', Carbohydrate Polymers, vol. 267, 118162 . https://doi.org/10.1016/j.carbpol.2021.118162 |
| ISSN: | 0144-8617 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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