Modification of chitosan by zincke reaction: synthesis of a novel polycationic chitosan-pyridinium derivative

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dc.creatorFernanda Jorge Gonçalves
dc.creatorRossimiriam Pereira de Freitas
dc.date.accessioned2024-08-05T14:09:30Z
dc.date.accessioned2025-09-09T01:10:34Z
dc.date.available2024-08-05T14:09:30Z
dc.date.issued2019
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
dc.format.mimetypepdf
dc.identifier.doihttps://doi.org/10.21577/0103-5053.20190135
dc.identifier.issn1678-4790
dc.identifier.urihttps://hdl.handle.net/1843/72545
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofJournal of the Brazilian Chemical Society
dc.rightsAcesso Aberto
dc.subjectQuitosana
dc.subjectMecanismos de reações orgânicas
dc.subjectBiopolímeros
dc.subjectRessonância magnética nuclear
dc.subject.otherChitosan
dc.subject.otherZincke reaction
dc.subject.otherPyridinium salts
dc.titleModification of chitosan by zincke reaction: synthesis of a novel polycationic chitosan-pyridinium derivative
dc.typeArtigo de periódico
local.citation.epage2323
local.citation.issue11
local.citation.spage2318
local.citation.volume30
local.description.resumoChitosan is a biodegradable aminopolysaccharide produced by deacetylation of acetamide groups of chitin, one of the most abundant organic materials in nature. Many different types of organic reactions have been described to modify the functional groups of chitosan and produce materials with applications in a large number of areas. However, the Zincke reaction, an old method which is commonly used to convert primary amine in pyridinium salts, has not been reported to transform the chitosan amino group at C-2 position in glucosamine units. In this paper, our efforts are described to carry out this reaction, employing different conditions to covalently anchor pyridinium salts on the polymer surface. Optimized synthesis conditions using water/ethanol as solvent, triethylamine and Zincke salt excess yielded a novel polycationic chitosan-pyridinium derivative with a weight gain of 52% after 48 h of reaction. The modified biopolymer is water insoluble and exhibits a high degree of chemical modification. The 13C solid state nuclear magnetic resonance (SS-NMR) spectrum of chitosan-pyridinium derivative showed signals at 147.0, 142.0 and 129.0 ppm, attributed to aromatic carbons, confirming the presence of a quaternary pyridinium ring directly attached to the biopolymer. The Zincke reaction was employed for the first time to modify the chitosan backbone.
local.identifier.orcidhttps://orcid.org/0000-0001-6974-3724
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://jbcs.sbq.org.br/pdf/2019-0136AR_BrazWoman

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