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Chitotriazolan (poly(β(1-4)-2-(1H-1,2,3-triazol-1-yl)-2-deoxy-d-glucose)) derivatives: Synthesis, characterization, and evaluation of antibacterial activity

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dc.contributor Háskóli Íslands
dc.contributor University of Iceland
dc.contributor.author Rathinam, Sankar
dc.contributor.author Hjálmarsdóttir, Martha Ásdís
dc.contributor.author Thygesen, Mikkel B.
dc.contributor.author Másson, Már
dc.date.accessioned 2021-11-19T16:17:04Z
dc.date.available 2021-11-19T16:17:04Z
dc.date.issued 2021-09-01
dc.identifier.citation Sankar Rathinam, Martha Á. Hjálmarsdóttir, Mikkel B. Thygesen, Már Másson, Chitotriazolan (poly(β(1-4)-2-(1H-1,2,3-triazol-1-yl)-2-deoxy-d-glucose)) derivatives: Synthesis, characterization, and evaluation of antibacterial activity, Carbohydrate Polymers, Volume 267, 2021, 118162, ISSN 0144-8617, https://doi.org/10.1016/j.carbpol.2021.118162.
dc.identifier.issn 0144-8617
dc.identifier.uri https://hdl.handle.net/20.500.11815/2718
dc.description.abstract Here we describe the first synthesis of a new type of polysaccharides derived from chitosan. In these structures, the 2-amino group on the pyranose ring was quantitively replaced by an aromatic 1,2,3-triazole moiety. The 2-amino group of chitosan and di-TBDMS chitosan was converted into an azide by diazo transfer reaction. The chitosan azide and TBDMS-chitosan azide were poorly soluble but could be fully converted to triazoles by “copper-catalysed Huisgen cycloaddition” in DMF or DMSO. The reaction could be done with different alkynes but derivatives lacking cationic or anionic groups were poorly soluble or insoluble in tested aqueous and organic solvents. Derivatives with N,N-dimethylaminomethyl, N,N,N-trimethylammoniummethyl, sulfonmethyl, and phosphomethyl groups linked to the 4-position of the triazole moiety were soluble in water at neutral or basic conditions and could be analyzed by 1H, 13C APT, COSY, and HSQC NMR. The quaternized cationic chitotriazolan's had high activity against S. aureus and E. coli, whereas the anionic chitotriazolan's lacked activity.
dc.description.sponsorship Rannsóknasjóður Rannís Rannsóknasjóður HÍ
dc.format.extent 118162
dc.language.iso en
dc.publisher Elsevier B.V.
dc.relation.ispartofseries Carbohydrate Polymers;267
dc.rights info:eu-repo/semantics/embargoedAccess
dc.subject Materials Chemistry
dc.subject Polymers and Plastics
dc.subject Organic Chemistry
dc.subject click chemistry
dc.subject Antimicrobial
dc.subject Chitosan
dc.subject Lífræn efnafræði
dc.title Chitotriazolan (poly(β(1-4)-2-(1H-1,2,3-triazol-1-yl)-2-deoxy-d-glucose)) derivatives: Synthesis, characterization, and evaluation of antibacterial activity
dc.type info:eu-repo/semantics/article
dcterms.license Aðgangur lokaður í 12 mánuði samkvæmt skilmálum útgefanda.
dc.description.version Final manuscript to publisher
dc.identifier.journal Carbohydrate Polymers
dc.identifier.doi 10.1016/j.carbpol.2021.118162
dc.contributor.department Lyfjafræðideild (HÍ)
dc.contributor.department Faculty of Pharmaceutical Sciences (UI)
dc.contributor.school Heilbrigðisvísindasvið
dc.contributor.school School of Health Sciences (UI)

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