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Precise synthesis of heterogeneous glycopolymers with well‐defined saccharide motifs in the side chain via post‐polymerization modification and recognition with lectin
Journal of Polymer Science ( IF 3.4 ) Pub Date : 2020-07-02 , DOI: 10.1002/pol.20200008
Meina Liu 1, 2, 3 , Dengyun Miao 1 , Xingyou Wang 1 , Caiyun Wang 1 , Wei Deng 1
Affiliation  

Heterogeneous glycopolymers with different sugar units in the side chain have been receiving considerable attention due to their potential properties in enhancing molecular recognition abilities toward a specific receptor, yet there are limited synthetic approaches to introduce different sugar motifs into the glycopolymer backbone. Herein, a series of heterogeneous glycopolymers consisting of different sugar units in the side chains were synthesized by post‐polymerization modification of activated PFPA ester precursor polymers. The functionalized amines bearing two different sugar motifs have been synthesized by gradient CuAAC reaction, which could serve as a platform for achieving heterogeneous sugar units with functional control in concise steps. Isothermal titration calorimetry (ITC) measurements of the obtained glycopolymers with Concanavalin A indicated that the heterogeneous glycopolymers, poly(Man‐βGlu‐OH) and poly(Man‐βGa‐OH) bearing αD‐mannose and other non‐binding β‐Glucose or β‐Galatose units, show higher affinities toward Concanavalin A in comparison to monoglycopolymer poly(Man‐Alkyne‐OH) in which the non‐binding sugar motifs was substituted with non‐sugar unit due to synergistic effects of non‐binding sugar units. Moreover, this work allows for precise fabrication of a broad variety of glycopolymers in which it significantly broadens the library of accessible polymer structures, either homogeneous or heterogeneous glycopolymers.

中文翻译:

通过聚合后修饰和凝集素识别,精确合成侧链上具有明确糖基序的异质糖聚合物

侧链上具有不同糖单元的异质糖聚合物由于其潜在的特性可以增强对特定受体的分子识别能力,因此受到了广泛的关注,但是将糖基引入不同的糖基骨架的合成方法有限。在此,通过活化PFPA酯前体聚合物的后聚合改性,合成了由侧链中不同糖单元组成的一系列异质糖聚合物。通过梯度CuAAC反应合成了带有两个不同糖基序的官能化胺,该胺可作为在简单步骤中实现功能控制的异构糖单元的平台。β的Glu-OH)和聚(人为β Ga的OH)轴承α - d -甘露糖和其它非结合β-葡萄糖或β-相比半乳糖单元,表现出对伴刀豆球蛋白A更高亲和力monoglycopolymer聚(曼-炔-OH),其中由于非结合糖单元的协同效应,非结合糖基序被非糖单元取代。而且,这项工作允许精确制造各种各样的糖聚合物,其中它大大拓宽了均质或非均质糖聚合物可及的聚合物结构的库。
更新日期:2020-07-02
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