In this report, we
present double-hydrophilic block glycopolymers
of poly(2-hydroxyethyl methacrylate)-b-poly(2-(β-glucosyloxy)ethyl
methacrylate) (PHEMA-b-PGEMA) and amphiphilic block
glycopolymers of poly(ethyl methacrylate)-b-PGEMA
(PEMA-b-PGEMA) synthesized via reversible addition–fragmentation
chain transfer (RAFT) polymerization. The block glycopolymers were
prepared in two compositions of P(H)EMA macro-chain transfer agents
(CTAs) and similar molecular weights of PGEMA. Structural analysis
of the resulting polymers as well as the conversion of (H)EMA and
GEMA monomers were determined by 1H NMR spectroscopy. Size
exclusion chromatography measurements confirmed both P(H)EMA macro-CTAs
and block glycopolymers had a low dispersity (Đ ≤ 1.5). The synthesized block glycopolymers had
a degree of polymerization and a molecular weight up to 222 and 45.3
kg mol–1, respectively. Both block glycopolymers
self-assembled into micellar structures in aqueous solutions as characterized
by fluorescence spectroscopy, ultraviolet–visible spectroscopy,
and dynamic light scattering experiments.
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, respectively. The majority of the bonds at the alpha position of acrylate units in oligocellulosyl-ethyl acrylate was fragmented as characterized by H 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.
β‐Glucosidase and horseradish peroxidase (HRP) are used as biocatalysts in aqueous solution for the enzymatic synthesis of glycomonomers and the respective enzymatic polymerization toward glycopolymers. The biocatalytically synthesized monomers contain (meth)acrylate functionalities that are able to be polymerized by an enzyme‐initiated polymerization using an HRP/hydrogen peroxide/acetylacetone ternary system. The structure of the glycomonomers and the respective glycopolymers as well as the monomer conversion after the reaction are determined by 1H NMR spectroscopy. The synthesized glycopolymers have a dispersity and a number‐average molecular weight up to 5.8 and 297 kg mol−1, respectively. Thermal and degradation properties of the glycopolymers are studied by differential scanning calorimetry and thermogravimetric analysis. In addition, preparation of glycopolymers via conventional free radical polymerization is performed and the properties of the obtained polymers are compared with the enzymatically synthesized glycopolymers.
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