Synthesis of thermoresponsive glycopolymers via ATRP of N-isopropylacrylamide and N-allylacrylamide and subsequent thiol-ene reaction

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• 作者：Christian von der Ehe ; Justyna A. Czaplewska ; Michael Gottschaldt ; Ulrich S. Schubert
• 关键词：Glycopolymer ; LCST ; Thiol&ndash ; ene reaction ; Lectin binding ; ATRP
• 刊名：European Polymer Journal
• 出版年：2013
• 出版时间：September, 2013
• 年：2013
• 卷：49
• 期：9
• 页码：2660-2669
• 全文大小：1202 K

文摘

To prepare thermoresponsive glycopolymers, new alkene functional copolymers based on N-isopropylacrylamide were synthesized and functionalized with sugar moieties. The copolymerization of N-isopropylacrylamide with N-allylacrylamide by ATRP led to soluble, well-defined polymers which were reacted with 1-thiosugars via a thiol-ene reaction. In addition to ¹H NMR spectroscopy, FT-IR spectroscopy, elemental analysis and size exclusion chromatography, the glycopolymers were characterized by turbidimetry, which revealed sharp and reversible coil-to-globule transitions of the prepared copolymers. Furthermore, lectin binding studies revealed the interaction of the galactosylated polymers to the lectin RCA₁₂₀ depending on their degree of functionalization. The results demonstrate that the discussed synthetic strategy represents a practical and flexible route towards functional N-isopropylacrylamide copolymers.