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Synthesis of neoglycopolymers by a combination of "click chemistry" and living radical polymerization
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Ladmiral, Vincent, Mantovani, Giuseppe, Clarkson, Guy J., Cauet, Solene, Irwin, Jacob L. and Haddleton, David M. (2006) Synthesis of neoglycopolymers by a combination of "click chemistry" and living radical polymerization. Journal of the American Chemical Society, 128 (14). pp. 4823-4830. doi:10.1021/ja058364k
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Official URL: http://dx.doi.org/10.1021/ja058364k
Abstract
The synthesis of novel well-defined alkyne side chain functional polymers featuring narrow molecular weight distributions (PDI = 1.09-1.17) by living radical polymerization is described. Grafting of protected and unprotected carbohydrates is achieved via either a C-6 or an anomeric azide (a or P) onto these polymers by Cu(I)-catalyzed "click chemistry", providing a simple and efficient route to synthetic glycopolymers. The strategy provides an extremely powerful tool for the synthesis of libraries of materials that differ only in the nature of the sugar moiety presented on a well-defined polymer scaffold. A library of multivalent ligands were then prepared following a "coclicking" synthetic protocol, and the reactivity of these glycopolymers in the presence of concanavalin A and Ricinus communis agglutinin, model lectins able to selectively bind appropriate mannose and galactose derivatives, respectively, was assessed.
Item Type: | Journal Item | ||||||
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Subjects: | Q Science > QD Chemistry | ||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||
Journal or Publication Title: | Journal of the American Chemical Society | ||||||
Publisher: | American Chemical Society | ||||||
ISSN: | 0002-7863 | ||||||
Official Date: | 22 March 2006 | ||||||
Dates: |
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Volume: | 128 | ||||||
Number: | 14 | ||||||
Number of Pages: | 8 | ||||||
Page Range: | pp. 4823-4830 | ||||||
DOI: | 10.1021/ja058364k | ||||||
Status: | Peer Reviewed | ||||||
Publication Status: | Published | ||||||
Access rights to Published version: | Restricted or Subscription Access |
Data sourced from Thomson Reuters' Web of Knowledge
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