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Issue 2, 2018
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Synthesis of (meth)acrylamide-based glycomonomers using renewable resources and their polymerization in aqueous systems

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Abstract

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.

Graphical abstract: Synthesis of (meth)acrylamide-based glycomonomers using renewable resources and their polymerization in aqueous systems

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Supplementary files

Article information


Submitted
06 Oct 2017
Accepted
10 Dec 2017
First published
14 Dec 2017

Green Chem., 2018,20, 476-484
Article type
Paper

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

A. Adharis, D. Vesper, N. Koning and K. Loos, Green Chem., 2018, 20, 476
DOI: 10.1039/C7GC03023A

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