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The effect of linker length on ConA and DC-SIGN binding of S-glucosyl functionalized poly(2-oxazoline)s†
Polymer Chemistry ( IF 4.6 ) Pub Date : 2017-12-27 00:00:00 , DOI: 10.1039/c7py01939d
Gokhan Yilmaz 1, 2, 3, 4, 5 , Veselina Uzunova 2, 3, 4, 6 , Manuel Hartweg 7, 8, 9, 10, 11 , Valentin Beyer 7, 8, 9, 10, 11 , Richard Napier 2, 3, 4, 6 , C. Remzi Becer 7, 8, 9, 10, 11
Affiliation  

A new monomer, 2-[2-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylthio)propyl)]-2-oxazoline (Ac4Glc-S-Ox), was synthesized by direct addition of 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose (Ac4Glc-SH) to 2-isopropenyl-2-oxazoline (iPOx) in the presence of solid butyl amine resin via a thiol–ene click reaction. The living cationic ring-opening polymerization was performed to prepare copolymers of Ac4Glc-S-Ox with 2-ethyl-2-oxazoline (EtOx). In order to systematically investigate the effect of the S-glucosyl substituent linked to the polymer backbone with different linkers on the cloud point and the binding ability, another series of glycopolymers was prepared by a post polymerization modification method. Copolymers of 2-decenyl-2-oxazoline and 2-butenyl-2-oxazoline with EtOx were first polymerized and then reacted with Ac4Glc-SH. The obtained glycopolymers exhibited lower critical solution temperature behavior that could be tuned easily by manipulating the alkyl linker length. Moreover, the binding results obtained using both turbidimetry and surface plasmon resonance techniques suggested that the relationship of the linker with the polymer backbone has a critical influence on glycopolymer–lectin binding behaviour.

中文翻译:

接头长度对S-葡萄糖基官能化聚(2-恶唑啉)s ConA和DC-SIGN结合的影响

一种新的单体,2- [2 - ((2,3,4,6-四ö乙酰基β- d -glucopyranosylthio)丙基)] - 2-恶唑啉(AC 4 Glc-小号-Ox),合成通过在固体存在下将2,3,4,6-四-O-乙酰基-1-硫代 - D-吡喃葡萄糖(Ac 4 Glc-SH)直接添加到2-异丙烯基-2-恶唑啉(iPOx)中丁胺树脂通过硫醇-烯的点击反应。进行活性阳离子开环聚合来制备的Ac共聚物4 Glc-小号与2-乙基-2-恶唑啉(ETOX)-Ox。为了系统地调查S的影响-葡糖基取代基在浊点和结合能力上通过不同的连接基连接到聚合物主链上,通过后聚合改性方法制备了另一系列的糖聚合物。首先使2-癸烯基-2-恶唑啉和2-丁烯基-2-恶唑啉与EtOx的共聚物聚合,然后与Ac 4 Glc-SH反应。所获得的糖聚合物表现出较低的临界溶液温度行为,可以通过操纵烷基接头长度来容易地对其进行调节。此外,使用比浊法和表面等离振子共振技术获得的结合结果表明,连接基与聚合物骨架之间的关系对糖聚合物-凝集素的结合行为具有至关重要的影响。
更新日期:2017-12-27
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