Abstract
Abstractβ‐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 by1H 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.
Highlights
The biocatalytically synthesized monomers containacrylate functionalities that are able to be polymerized by an enzyme-initiated polymerization using an horseradish peroxidase (HRP)/hydrogen work was extended in recent years to continue the efforts of the Stadler group.[15,16,17,18,19,20,21,22,23,24,25,26,27,28,29]
We present an HRP-mediated synthesis of glycopolymers at room temperature in aqueous solution
The enzymatic polymerization of glycomonomers was performed at 25 °C while the conventional reaction was done at 50 °C
Summary
2-Hydroxyethyl acrylate (HEA) 96%, 2-hydroxyethyl methacrylate (HEMA) 97%, β-glucosidase from almonds (activity ≥2 units mg−1 solid), and peroxidase from HRP type I (MW ≈ 44 kDa) with an activity of 88 pyrogallol units mg−1 solid were purchased from Sigma-Aldrich. One pyrogallol unit was defined as the amount of enzyme that converts pyrogallol to 1.0 mg purpurogallin in 20 s (pH: 6.0, temperature: 20 °C). 4-Hydroxybutyl acrylate (HBA) 95% was acquired from ABCR Chemicals. Acetylacetone (ACAC) 99+%, α-d(+)-glucose ≥99%, potassium persulfate (KPS) 99+%, 1,4-dioxane, and hydrogen peroxide (H2O2) 35 wt% solution in water was obtained from Acros Organics. Chloroform (CHCl3), and methanol (MeOH) were acquired from Biosolve BV.
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