Environmentally friendly pathways towards the synthesis of vinyl-based oligocelluloses

Azis Adharis, Dejan M. Petrović, Ibrahim Özdamar, Albert J.J. Woortman, Katja Loos

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

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.
Original languageEnglish
Pages (from-to)196-204
Number of pages9
JournalCarbohydrate Polymers
Volume193
Early online date30-Mar-2018
DOIs
Publication statusPublished - 1-Aug-2018

Keywords

  • Enzymatic synthesis
  • Cellodextrin phosphorylases
  • Reverse phosphorolysis
  • Vinyl glucosides
  • Renewable resources
  • Functionalized oligocelluloses
  • UNMODIFIED CELLO-OLIGOSACCHARIDES
  • ENZYMATIC-SYNTHESIS
  • CELLODEXTRIN PHOSPHORYLASE
  • CELLULOSE OLIGOMERS
  • DIBLOCK COPOLYMERS
  • IN-VITRO
  • CO-OLIGOMERS
  • NANOPARTICLES
  • POLYMERIZATION
  • THERMOCELLUM

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