Synthesis of Neoglycopolymers by a Combination of "Click Chemistry" and Living Radical Polymerization
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- 作者：Vincent Ladmiral ; Giuseppe Mantovani ; Guy J. Clarkson ; Solene Cauet ; Jacob L. Irwin ; and David M. Haddleton
- 刊名：Journal of the American Chemical Society
- 出版年：2006
- 出版时间：April 12, 2006
- 年：2006
- 卷：128
- 期：14
- 页码：4823 - 4830
- 全文大小：242K
- 年卷期：v.128,no.14(April 12, 2006)
- ISSN：1520-5126
文摘
The synthesis of novel well-defined alkyne side chain functional polymers featuring narrowmolecular weight distributions (PDI = 1.09-1.17) by living radical polymerization is described. Grafting ofprotected and unprotected carbohydrates is achieved via either a C-6 or an anomeric azide (
or 
) ontothese polymers by Cu(I)-catalyzed "click chemistry", providing a simple and efficient route to syntheticglycopolymers. The strategy provides an extremely powerful tool for the synthesis of libraries of materialsthat differ only in the nature of the sugar moiety presented on a well-defined polymer scaffold. A library ofmultivalent ligands were then prepared following a "coclicking" synthetic protocol, and the reactivity of theseglycopolymers in the presence of concanavalin A and Ricinus communis agglutinin, model lectins able toselectively bind appropriate mannose and galactose derivatives, respectively, was assessed.
or ) ontothese polymers by Cu(I)-catalyzed "click chemistry", providing a simple and efficient route to syntheticglycopolymers. The strategy provides an extremely powerful tool for the synthesis of libraries of materialsthat differ only in the nature of the sugar moiety presented on a well-defined polymer scaffold. A library ofmultivalent ligands were then prepared following a "coclicking" synthetic protocol, and the reactivity of theseglycopolymers in the presence of concanavalin A and Ricinus communis agglutinin, model lectins able toselectively bind appropriate mannose and galactose derivatives, respectively, was assessed.