Simple method for ultrasound assisted «click» modification of azido-chitosan derivatives by CuAAC

Simple method for ultrasound assisted «click» modification of azido-chitosan derivatives by CuAAC

New quaternized chitosan derivatives HT-TMC were synthesized as a result of copper catalyzed azide-alkyne [3 + 2] cycloaddition (CuAAC). The structure of the HT-TMC was verified by 2D NMR. The synthesis was carried out as a result of the formation of Cu(I) in situ, under the action of ultrasound in...

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Veröffentlicht in:Carbohydrate polymers 2022-04, Vol.282, p.119109-119109, Article 119109
Hauptverfasser: Lunkov, Alexey, Shagdarova, Balzhima, Lyalina, Tatiana, Dubinnyi, Maxim A., Karpova, Natalia, Lopatin, Sergey, Il'ina, Alla, Varlamov, Valery
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Antimicrobial activity
Chitosan
Click chemistry
Quaternary chitosan
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container_end_page 119109
container_issue
container_start_page 119109
container_title Carbohydrate polymers
container_volume 282
creator Lunkov, Alexey
Shagdarova, Balzhima
Lyalina, Tatiana
Dubinnyi, Maxim A.
Karpova, Natalia
Lopatin, Sergey
Il'ina, Alla
Varlamov, Valery
description New quaternized chitosan derivatives HT-TMC were synthesized as a result of copper catalyzed azide-alkyne [3 + 2] cycloaddition (CuAAC). The structure of the HT-TMC was verified by 2D NMR. The synthesis was carried out as a result of the formation of Cu(I) in situ, under the action of ultrasound in aerobic conditions in the presence of acetic acid and metallic copper (copper turnings). The new derivatives were characterized by increased pH range of solubility (DS range 18–76%) and the presence of antibacterial and fungicidal activities. The proposed catalytic system makes it possible to easily and efficiently obtain new derivatives of chitosan as a result of ultrasound-promoted CuAAC. [Display omitted] •New cationic derivatives of chitosan (HT-TMC) were synthesized.•CuAAC reaction was carried out under ultrasound using new Сu0/AcOH catalytic system.•Benefits of the new catalytic system for «click» modification were demonstrated.•Biological activity of HT-TMC derivatives was studied.
doi_str_mv 10.1016/j.carbpol.2022.119109
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source ScienceDirect Journals (5 years ago - present)
subjects Antimicrobial activity
Chitosan
Click chemistry
Quaternary chitosan
title Simple method for ultrasound assisted «click» modification of azido-chitosan derivatives by CuAAC
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