Water-soluble triazole chitin derivative and its based nanoparticles: Synthesis, characterization, catalytic and antibacterial properties

• Published in: Carbohydrate polymers Vol. 257; p. 117593
• Main Authors: Kritchenkov, Andreii S., Egorov, Anton R., Abramovich, Rimma A., Kurliuk, Aleh V., Shakola, Tatsiana V., Kultyshkina, Ekaterina K., Ballesteros Meza, Moises J., Pavlova, Anastasia V., Suchkova, Elena P., Le Nhat Thuy, Giang, Van Tuyen, Nguyen, Khrustalev, Victor N.
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01-04-2021
• Subjects: Aldol reaction; Azido chitin derivatives; Chitin; Click-chemistry; Ionic gelation method; Nanoparticles; Ionic gelation method; Lithium chloride; Tripolyphosphate (TPP); Chitin; Aldol reaction; Propargylic ester of N,N,N-trimethyl glycine; diisopropylethylamine (DIEA); Click-chemistry; Propargyl alcohol; Copper(II) sulfate pentahydrate; Nanoparticles; Betaine; Thionyl chloride 2-(azidomethyl)oxirane; Chitosan; Azido chitin derivatives
• ISSN: 0144-8617; 1879-1344
• DOI: 10.1016/j.carbpol.2020.117593

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•The treatment of chitin with 2-(azidomethyl)oxirane yields azido chitin derivatives.•The azido chitin derivatives undergo CuAAC to give triazole chitin derivatives.•The triazole chitin derivatives are water-soluble and non-toxic.•The derivatives are catalysts in aldol reaction and possess antibacterial effect.
In this work, we treated chitin with 2-(azidomethyl)oxirane and successfully involved the resultant azido chitin derivatives in the ultrasound-assisted Cu(I)-catalyzed azido-alkyne click (CuAAC) reaction with propargylic ester of N,N,N-trimethyl glycine. Thus, we obtained novel water-soluble triazole chitin derivatives. The triazole chitin derivatives and their nanoparticles are characterized by a high in vitro antibacterial activity, which is the same or even higher than that of commercial antibiotics ampicillin and gentamicin. The obtained derivatives are non-toxic. Moreover, the obtained water-soluble polymers are highly efficient green catalysts for the aldol reaction in green solvent water. The catalysts can be easily extracted from the reaction mixture by its precipitation with green solvent ethanol followed by centrifugation and they can be reused at least 10 times.