Literature DB >> 32505997

Greener approach for synthesis of N,N,N-trimethyl chitosan (TMC) using ternary deep eutectic solvents (TDESs).

Tushar Mahajan1, Prachi Bangde2, Prajakta Dandekar3, Ratnesh Jain4.   

Abstract

N,N,N-trimethyl chitosan (TMC), quaternized hydrophilic derivative of chitosan, has been projected to have wide applications in the pharmaceutical industry owing to its improved solubility at physiological conditions. However, the conventional synthesis of TMC involves toxic organic agents, which complicates its use for biological applications. Moreover, these reactions result into unwanted O-methylation and scission of the parent polymer. In the present study we have addressed these limitations by employing a green approach to synthesize TMC, by using lipase as the biocatalyst and dimethyl carbonate (DMC) as the green methylating agent, in a reaction medium comprising of ternary deep eutectic solvents (TDESs). Synthesis of TMC was carried out by using two different lipases from Burkholderia cepacia and Candida rugosa. The resulting TMC was characterized by using FTIR, 1H NMR, DSC, XRD. Methylation was confirmed by FTIR analysis (-CH at 1666 cm-1) and 1H NMR (?? = 3.3 ppm). DSC study revealed a lower thermal stability of TMC as compared to chitosan. These results indicated the possibility of using DMC as a green methylating agent, along with TDESs as green and sustainable solvents, for lipase catalyzed reactions. TMC was successfully synthesized and exhibited a degree of quaternization of about 12.5%, 15.69%, when synthesized used lipases from Burkholderia cepacia and Candida rugosa, respectively.
Copyright © 2020 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Dimethyl carbonate; Green synthesis; Lipase enzyme; Ternary deep eutectic solvents (TDESs); Trimethyl chitosan (TMC)

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Year:  2020        PMID: 32505997     DOI: 10.1016/j.carres.2020.108033

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN: 0008-6215            Impact factor:   2.104


  2 in total

1.  Self-Assembly of Soluble Chitosan Derivatives Nanoparticles for Vaccine: Synthesis, Characterization and Evaluation.

Authors:  Jinbao Liu; Shuang Yu; Wanying Qu; Zheng Jin; Kai Zhao
Journal:  Polymers (Basel)       Date:  2021-11-25       Impact factor: 4.329

2.  Preparation, Characterization, and Bio Evaluation of Fatty N- Hexadecanyl Chitosan Derivatives for Biomedical Applications.

Authors:  Hanaa Mansour; Samia El-Sigeny; Sarah Shoman; Marwa M Abu-Serie; Tamer M Tamer
Journal:  Polymers (Basel)       Date:  2022-09-25       Impact factor: 4.967

  2 in total

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