Protecting-Group-Free Synthesis of Glycopolymers Bearing Thioglycosides via One-Pot Monomer Synthesis from Free Saccharides
Protecting-Group-Free Synthesis of Glycopolymers Bearing Thioglycosides via One-Pot Monomer Synthesis from Free Saccharides
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通过游离糖一锅法单体合成无保护基团合成带有硫代糖苷的糖聚合物
DOI：
10.1002/pola.27417
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发表时间：
2014
期刊：
影响因子：
--
通讯作者：
Y. Kimura
中科院分区：
文献类型：
--
作者：
T. Tanaka;G. Inoue;S. Shoda;Y. Kimura
具有硫代糖苷侧基的聚丙烯酰胺成功地由硫代糖苷单体合成，所述硫代糖苷单体通过一锅法容易地制备，而无需对起始游离糖苷上的羟基进行任何保护。通过使用2-氯-1，3-二甲基咪唑啉氯化物和4-氨基苯并酚直接合成硫代糖苷，然后进行丙烯酰胺化，合成糖单体。通过可逆加成-断裂链转移聚合，使用三硫代碳酸酯衍生物作为链转移剂，将它们与丙烯酰胺共聚成糖共聚物。由于在水溶液中凝集素与蛋白质之间的多价相互作用，用巯基封端的糖共聚物固定的金纳米颗粒和金涂覆的石英晶体微天平传感器对相应的凝集素表现出高亲和力。© 2014 Wiley Periodicals，Inc. J. Polym.科学，部分A：聚合物。Chem.2014，52，3513-3520
Polyacrylamides having pendant thioglycosides were successfully synthesized from thioglycosidic monomers that were readily prepared by one‐pot method without any protection of the hydroxy groups on the starting free saccharides. The glycomonomers were synthesized by the direct synthesis of thioglycosides using 2‐chloro‐1,3‐dimethylimidazolinium chloride and 4‐aminobenzentiol, and the following acrylamidation. They were co‐polymerized with acrylamide into glycopolymers by reversible addition‐fragmentation chain transfer polymerization using a trithiocarbonate derivative as a chain transfer agent. The gold nanoparticles and gold‐coated quartz crystal microbalance sensor immobilized with the thiol‐terminated glycopolymers exhibited high affinity for the corresponding lectins due to multivalent interaction between saccharides and protein in aqueous solution. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem.2014,52, 3513–3520