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Chemoenzymatic polycondensation of para-benzylamino phenol

  • Pinar Yildirim , Ersen Gokturk , Ersen Turac , Haci O Demir und Ertugrul Sahmetlioglu EMAIL logo
Veröffentlicht/Copyright: 11. Februar 2016
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Chemical Papers
Aus der Zeitschrift Chemical Papers Band 70 Heft 5

para-Benzylamine substituted oligophenol was synthesized via enzymatic oxidative polycondensation of 4-(benzylamino)phenol (BAP). Polymerization involved only the phenolic moiety without oxidizing the sec-amine (benzylamine) group. Chemoselective polycondensation of BAP monomer using HRP enzyme yielded oligophenol with sec-amine functionality on the side-chain. Effects of various factors including solvent system, reaction pH and temperature on the polycondensation were studied. Optimum polymerization process with the highest yield (63 %) and molecular weight (Mn = 5000, degree of polymerization ≈ 25) was achieved using the EtOH/ buffer (pH 5.0; 1 : 1 vol. ratio) at 25 °C in 24 h under air. Characterization of the oligomer was accomplished by 1H NMR and 13C NMR, Fourier transform infrared spectroscopy (FT-IR), gel permeation chromatography (GPC), ultraviolet-visible spectroscopy (UV-Vis), cyclic voltammetry (CV) and thermogravimetric analysis (TGA). The polymerization process involved the elimination of hydrogen from BAP, and phenolic-OH end groups of the oligo(BAP), confirmed using 1H NMR and FT-IR analyses. The oligomer backbone possessed phenylene and oxyphenylene repeat units, and the resulting oligomer was highly soluble in common organic solvents such as acetone, CHCl3, 1,4-dioxane, N,N-dimethylformamide (DMF), tetrahydrofurane (THF) and dimethylsulfoxide (DMSO). Oligo(BAP) was thermally stable and exhibited 5 % and 50 % mass loss determined by thermogravimetric analysis at 247°C and 852°C, respectively.

Keywords: enzymatic oxidative polymerization; horseradish peroxidase enzyme; oligophenol; hydrogen peroxide

Acknowledgements.

Ersen Gokturk would like to acknowledge the Turkish Ministry of National Education for his Ph.D. scholarship.

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Received: 2015-7-31
Revised: 2015-10-6
Accepted: 2015-10-7
Published Online: 2016-2-11
Published in Print: 2016-5-1

© 2015 Institute of Chemistry, Slovak Academy of Sciences

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https://doi.org/10.1515/chempap-2015-0242
Schlagwörter für diesen Artikel
enzymatic oxidative polymerization; horseradish peroxidase enzyme; oligophenol; hydrogen peroxide

Artikel in diesem Heft

  1. Original Paper
  2. Preparation and characterisation of gelatine hydrogels predisposed to use as matrices for effective immobilisation of biocatalystst‡
  3. Original Paper
  4. Photocatalytic reduction of nitro aromatic compounds to amines using a nanosized highly active CdS photocatalyst under sunlight and blue LED irradiation
  5. Original Paper
  6. Synthesis of butyrate using a heterogeneous catalyst based on polyvinylpolypyrrolidone
  7. Original Paper
  8. Behaviour of selected pesticide residues in blackcurrants (Ribes nigrum) during technological processing monitored by liquid-chromatography tandem mass spectrometry
  9. Original Paper
  10. Influence of solvents and novel extraction methods on bioactive compounds and antioxidant capacity of Phyllanthus amarus
  11. Original Paper
  12. Investigation of phytochemicals and antioxidant capacity of selected Eucalyptus species using conventional extraction
  13. Original Paper
  14. Innovative approach to treating waste waters by a membrane capacitive deionisation system
  15. Original Paper
  16. Liquid—liquid equilibria of ternary systems of 1-hexene/hexane and extraction solvents
  17. Original Paper
  18. Design of extractive distillation process with mixed entraineri‡
  19. Original Paper
  20. Kinetic study of non-reactive iron removal from iron-gall inks
  21. Original Paper
  22. Chemoenzymatic polycondensation of para-benzylamino phenol
  23. Original Paper
  24. Copper corrosion behaviour in acidic sulphate media in the presence of 5-methyl-lH-benzotriazole and 5-chloro-lH-benzotriazole
  25. Original Paper
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  27. Original Paper
  28. Design, synthesis and anti-mycobacterial evaluation of some new iV-phenylpyrazine-2-carboxamides
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  30. Convenient amidation of carboxyl group of carboxyphenylboronic acids
  31. Short Communication
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  33. Erratum
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  36. Erratum to “Martyna Rzelewska, Monika Baczyńska, Magdalena Regel-Rosocka, Maciej Wiśniewski: Trihexyl(tetradecyl)phosphonium bromide as extractant for Rh(III), Ru(III) and Pt(IV) from chloride solutions”, Chemical Papers 70 (4) 454–460 (2016)*
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