Formation of highly quaternized N,N,N-trimethylchitosan: a chemoselective methodology in aqueous media

Autor: Caroline Dion, Youssouf Djibril Soubaneh, Steeven Ouellet, Jonathan Gagnon
Rok vydání: 2019
Předmět:
Zdroj: Pure and Applied Chemistry. 91:489-496
ISSN: 1365-3075
0033-4545
DOI: 10.1515/pac-2018-0924
Popis: N,N,N-Trimethylchitosan (TMC) represents a rare example of cationic polysaccharides and numerous studies have shown its potential in biological and biomedical applications. TMC with high degrees of quaternization (DQ) were synthesized from N-methylation of N,N-dimethylchitosan (DMC), which was obtained by reductive alkylation of high molecular weight chitosan in a simple step process and in good yields. The effects of base and solvents were evaluated on the quaternization reaction. The N-methylation of DMC was performed selectively by CH3I and carbonate in water where quaternization was achieved quantitatively with a low degree of O-methylation (17 %). Moreover, the greener procedure allows easy recovery and purification by conventional filtration as a carbonate salt, in which the anion can be exchanged by an acid-base reaction. Quantification of DQ involving 1H NMR integration of methyl peaks must be performed on protonated TMC. High field NMR spectra of TMC showed two specific chemical shifts for anomeric peaks (5.0 and 5.4 ppm) that can also be used for the determination of DQ. This latter method avoids the superimposition problems with other pyranosyl peaks.
Databáze: OpenAIRE
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