Water-Soluble Quaternary and Protonable Basic Chitotriazolans: Synthesis by Click Chemistry Conversion of Chitosan Azides and Investigation of Antibacterial Activity

• Published in: Journal of functional biomaterials Vol. 15; no. 3; p. 63
• Main Authors: Rathinam, Sankar, Magdadaro, Romano, Hjálmarsdóttir, Martha Á, Másson, Már
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 01.03.2024; MDPI
• Subjects: Alkynes; Amino groups; Ammonium; Antibacterial activity; Antibacterial agents; Antimicrobial agents; Azide; Bacteria; Basic converters; Chemical synthesis; Chemistry; Chitosan; click chemistry; Copper; Copper converters; Cycloaddition; E coli; Escherichia coli; Magnetic resonance spectroscopy; NMR spectroscopy; Nuclear magnetic resonance spectroscopy; Peptides; Polymerization; Polymers; Sodium; Staphylococcus aureus; Toxicity; triazole; Triazoles; Water chemistry; United Kingdom; Germany; United States > US; antibacterial activity; chitosan; click chemistry; triazole
• ISSN: 2079-4983; 2079-4983
• DOI: 10.3390/jfb15030063

The azide transfer reaction and copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) can be used to convert the amino groups in chitosan to triazole 1,2,3-moieties. The resulting polymer has been named chitotriazolan. This synthesis was performed with six different quaternary ammonium alkynes and three amine alkynes to obtain a series of nine water-soluble chitotriazolan derivatives. The structure and complete conversion of the azide were confirmed by FT-IR and proton NMR spectroscopy. The derivatives were investigated for antibacterial activity against , , , and The activity of the quaternized chitotriazolan derivatives varied depending on the structure of the quaternary moiety and the species of bacteria. The basic protonable derivatives were less active or inactive against the bacteria.