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Synthesis and unambiguous NMR characterization of linear and branched N-alkyl chitosan derivatives.
Van Poucke, Casper; Verdegem, Evert; Mangelinckx, Sven; Stevens, Christian V.
Afiliación
  • Van Poucke C; Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
  • Verdegem E; Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
  • Mangelinckx S; Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
  • Stevens CV; Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium. Electronic address: chris.stevens@ugent.be.
Carbohydr Polym ; 337: 122131, 2024 Aug 01.
Article en En | MEDLINE | ID: mdl-38710547
ABSTRACT
Chitosan, sourced from abundant chitin-rich waste streams, emerges as a promising candidate in the realm of future functional materials and chemicals. While showing numerous advantageous properties, chitosan sometimes falls short of competing with today's non-renewable alternatives. Chemical derivatization, particularly through N-alkylation, proves promising in enhancing hydrophobic functionalities. This study synthesizes fifteen chitosan derivatives (degree of substitution = 2-10 %) using an improved reductive amination method. Next, selective depolymerization through acid hydrolysis reduced the chain rigidity imposed by the polymer backbone. This facilitated unambiguous structural characterization of the synthesized compounds using a combination of common NMR techniques. Two potential side reactions are identified for the first time, emphasizing the need for detailed structural information to unlock the true potential of these derivatives in future applications.

HYPOTHESIS:

The increase in chain mobility induced by the selective depolymerization of aliphatic N-alkyl chitosan derivatives allows for an unambiguous NMR characterization.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Carbohydr Polym Año: 2024 Tipo del documento: Article País de afiliación: Bélgica Pais de publicación: Reino Unido
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Carbohydr Polym Año: 2024 Tipo del documento: Article País de afiliación: Bélgica Pais de publicación: Reino Unido