Neoglycopolymers based on 4-vinyl-1,2,3-triazole monomers prepared by click chemistry

Hetzer, M., Chen, G., Barner-Kowollik, C., & Stenzel, M. H. (2010) Neoglycopolymers based on 4-vinyl-1,2,3-triazole monomers prepared by click chemistry. Macromolecular Bioscience, 10(2).

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The synthesis of a new glycomonomer based on mannose, prepared via CuAAC, is reported. The resulting 1,2,3-triazole linkage between mannose and the polymer backbone ensures the formation of highly stable glycopolymers, which will not undergo hydrolysis. The monomer 2′-(4-vinyl-[1,2,3]-triazol-1-yl) ethyl-O-α-D-mannopyranoside was polymerized in the presence of a RAFT agent - 3-benzylsulfanylthiocarbonylsulfanyl propionic acid - to yield well-defined polymers with molecular weights up to 51 500 g mol-1 and a PDI of 1.16. The resulting polymer was employed as a macroRAFT agent in the polymerization of NIPAAm in order to generate thermo-responsive block copolymers, which undergo reversible micelle formation at elevated temperatures. The rapid interaction between the polymers prepared and ConA confirms the high affinity of these structures to proteins. While the linear glycopolymers already undergo a fast complexation with ConA, the reported rates have found to be exceeded by the micellar glycopolymer structure presented in the current contribution. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA.

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ID Code: 99243
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :46
Export Date: 5 September 2016
Correspondence Address: Stenzel, M. H.; Centre for Advanced Macromolecular Design (CAMD), School of Chemical Sciences and Engineering, University of New South Wales, Sydney, NSW, Australia; email:
Chemicals/CAS: triazole, 37306-44-8; 2-(4-vinyl-(1,2,3)-triazol-1-yl)ethyl-O-mannopyranoside; Mannosides; Polymers; Polysaccharides; Triazoles; Vinyl Compounds
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Keywords: Click chemistry, Glycopolymer, Micelles, Reversible addition fragmentation chain transfer (RAFT), Elevated temperature, Glycopolymers, High affinity, Macro-RAFT agent, Micelle formation, Neoglycopolymers, Polymer backbones, Propionic acids, RAFT agents, Reversible addition fragmentation chain transfer, Thermo-responsive, Block copolymers, Complexation, Fatty acids, Monomers, Nitrogen compounds, Free radical polymerization, copolymer, triazole, article, chemical interaction, chemical structure, complex formation, hydrolysis, molecular weight, polymerization, synthesis, Chemistry, Organic, Chromatography, Gel, Mannosides, Nephelometry and Turbidimetry, Polymers, Polysaccharides, Spectrophotometry, Ultraviolet, Triazoles, Vinyl Compounds
DOI: 10.1002/mabi.200900199
ISSN: 16165187
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 07 Oct 2016 02:58

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