Synthesis of (meth)acrylamide-based glycomonomers using renewable resources and their polymerization in aqueous systems,Green Chemistry

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Synthesis of (meth)acrylamide-based glycomonomers using renewable resources and their polymerization in aqueous systems
Green Chemistry ( IF 9.3 ) Pub Date : 2017-12-14 00:00:00 , DOI: 10.1039/c7gc03023a
Azis Adharis _{1,

2,

3,

4,

5} , Dennis Vesper _{1,

2,

3,

4,

5} , Nick Koning _{1,

2,

3,

4,

5} , Katja Loos _{1,

2,

3,

4,

5}

Affiliation

In this work, we present the kinetically-controlled enzymatic synthesis of novel glycosyl-(meth)acrylamide monomers using β-glucosidase. Cellobiose served as the glycosyl donor in the enzyme catalyzed transglycosylation reaction and hydroxyl-alkyl (meth)acrylamides as the glycosyl acceptor. After optimization, we were able to increase the glycomonomer yield up to 68% by changing the glycosyl donor to p-nitrophenyl β-D-glucopyranoside and adding BMIMPF₆ as cosolvent. The structure of the glycomonomers was confirmed by ¹H NMR, ¹³C NMR, and mass spectrometry experiments. Aqueous RAFT polymerization of the glycomonomers was successfully performed resulting in glycopolymers with molecular weights up to 30 kg mol⁻¹ and relatively low polydispersity indices (PDI's < 1.30). Free radical polymerization of the glycomonomers was executed as well with the obtained glycopolymers resulting in higher molecular weights and PDI's than the glycopolymers prepared by RAFT polymerization. Thermal properties of the synthesized glycopolymers were investigated via differential scanning calorimetry.

中文翻译：

利用可再生资源合成（甲基）丙烯酰胺基糖单体及其在水性体系中的聚合

在这项工作中，我们介绍了使用β-葡萄糖苷酶的新型糖基-（甲基）丙烯酰胺单体的动力学合成方法。纤维二糖在酶催化的转糖基化反应中充当糖基供体，羟烷基（甲基）丙烯酰胺作为糖基受体。优化后，我们可以通过将糖基供体更改为对硝基苯基β- D-吡喃葡萄糖苷并添加BMIMPF ₆作为助溶剂，将糖单体的产率提高至68％。糖单体的结构通过¹ H NMR，¹³ C NMR和质谱实验确认。成功地进行了糖单体的RAFT水溶液聚合，得到了分子量高达30 kg mol的糖聚合物^-1和相对较低的多分散指数（PDI <1.30）。糖单体的自由基聚合也与所获得的糖聚合物一起进行，从而得到比通过RAFT聚合制备的糖聚合物更高的分子量和PDI。通过差示扫描量热法研究了合成的糖聚合物的热性质。

更新日期：2018-01-22

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