Environmentally friendly pathways towards the synthesis of vinyl-based oligocelluloses

Carbohydrate Polymers
Azis AdharisKatja Loos

Abstract

The synthesis of vinyl-based oligocelluloses using cellodextrin phosphorylase as biocatalyst in buffer solution is presented. Various types of vinyl glucosides bearing (meth)acrylates/(meth)acrylamides functionalities served as the glucosyl acceptor in the enzyme catalyzed reverse phosphorolysis reaction and α-glucose 1-phosphate as the glucosyl donor. The enzymatic reaction was followed by thin layer chromatography and the isolated product yields were about 65%. The synthesized vinyl-based oligocelluloses had an average number of repeating glucosyl units and a number average molecular weight up to 8.9 and 1553 g mol-1, respectively. The majority of the bonds at the alpha position of acrylate units in oligocellulosyl-ethyl acrylate was fragmented as characterized by 1H NMR spectroscopy and MALDI-ToF spectrometry. Nevertheless, a minor amount of fragmentation was observed in oligocellulosyl-ethyl methacrylate and oligocellulosyl-butyl acrylate but no fragmentation was detected in the (meth)acrylamide-based oligocelluloses. Crystal lattice of the prepared vinyl-based oligocelluloses was investigated via wide-angle X-ray diffraction experiments.

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Citations

Nov 5, 2019·Biotechnology Journal·Chao Zhong, Bernd Nidetzky
Apr 29, 2021·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Yuuki Hata, Takeshi Serizawa
Feb 6, 2020·ACS Omega·Pia SkoczinskiKatja Loos
Aug 16, 2021·Carbohydrate Research·Gregory S BulmerJolanda M van Munster
Sep 8, 2021·ACS Biomaterials Science & Engineering·Xin ZhangHoward Wang

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