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Synthesis of poly(4-aminosalicylic acid) through enzymatic and oxidative polycondensation by H2O2 oxidant

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Abstract

Aromatic compounds containing hydroxyl and amine groups in their structure are converted into oligomers or polymers through oxidative polymerization in water or organic solvent media. Again, aromatic amine or aromatic hydroxyl compounds are converted into oligomers or polymers by horseradish peroxidase (HRP) enzyme at different pH values in water or organic solvent media. Since the enzymatic oligomerization or polymerization of such compounds is environmentally sensitive, they are referred to as green chemistry. Poly(4-aminosalicylic acid) was synthesized by both enzymatic (PASA-E) and oxidative polycondensation (PASA-O) reactions. The structure and characterization were determined by FTIR, UV–vis, NMR, TGA, fluorescence and SEM measurements.PASA-O from 4-aminosalicylic acid was obtained by chemical oxidative polycondensation in glacial acetic acid by H2O2 (35% aqueous solution) as an oxidant. Enzymatic oxidative polymerizationof 4-aminosalicylic acid was performed by HRP. It has important advantages such as mild reaction conditions, mainly in terms of temperature and toxicity.The optical bandgap (Eg) values of ASA, PASA-O and PASA-E polymers were calculated to be 3.72, 2.40, and 2.73 eV, respectively. The electrochemical properties of compounds were determined by CV. The electrochemical bandgap (E′g) values of PASA-O and PASA-E were determined as 2.16 and 2.68 eV, respectively. The residual amount of PASA-O was higher than that of ASA and PASA-E at 1000 °C.

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References

  1. Suyal K, Joshi N, Rautela JH, Pant S (2010) Fluorescence properties of 4-amino salicylic acid in polymers. J Photochem Photobiol A 216:51–58

    Article  CAS  Google Scholar 

  2. German N, Popov A, Ramanaviciene A, Ramanavicius A (2017) Evaluation of enzymatic formation of polyaniline nanoparticles. Polymer 115:211–216

    Article  CAS  Google Scholar 

  3. Ramanavicius S, Ramanavicius A (2021) Conducting polymers in the design of biosensors and biofuel cells. Polymers 13:49

    Article  CAS  Google Scholar 

  4. Ramanavicius S, Ramanavicius A (2021) Charge transfer and biocompatibility aspects in conducting polymer-based enzymatic biosensors and biofuel cells. Nanomaterials 11:371

    Article  CAS  Google Scholar 

  5. Uyama H, Kobayashi S (2002) Enzyme-catalyzed polymerization to functional polymers. J Mol Catal B Enzym 19:117–127

    Article  Google Scholar 

  6. Pakalapati H, Tariq M, Arumugasamy S (2019) Optimization and modelling of enzymatic polymerization of ε-caprolactone to polycaprolactone using candida antartica lipase B with response surface methodology and artificial neural network. Enzyme Microb Technol 122:7–18

    Article  CAS  Google Scholar 

  7. Krikstolaityte V, Kuliesius J, Ramanaviciene A, Mikoliunaite L, Kausaite-Minkstimiene A, Oztekin Y, Ramanavicius A (2014) Enzymatic polymerization of polythiophene by immobilized glucose oxidase. Polymer 55:1613–1620

    Article  CAS  Google Scholar 

  8. Oshima T, Sato M, Shikaze Y, Ohto K, Inoue K, Baba Y (2007) Enzymatic polymerization of o-phenylendiamine with cytochrome c activated by a calixarene derivative in organic media. Biochem Eng J 35:66–70

    Article  CAS  Google Scholar 

  9. Huerta-Miranda G, Arrocha-Arcos A, Miranda-Hernandez M (2018) Gold nanoparticles/4-aminothiophenol interfaces for direct electron transfer of horseradish peroxidase: enzymatic orientation and modulation of sensitivity towards hydrogen peroxide detection. Bioelectrochemistry 122:77–83

    Article  CAS  Google Scholar 

  10. Kim Y, Shibata K, Uyama H, Kobayashi S (2008) Synthesis of ultrahigh molecular weight phenolic polymers by enzymatic polymerization in the presence of amphiphilictriblock copolymer in water. Polymer 49:4791–4795

    Article  CAS  Google Scholar 

  11. Kausaite-Minkstimiene A, Ramanaviciene A, Simanaityte R, Gabrielaitis D, Glumbokaite L, Ramanavicius A (2015) Evaluation of poly(pyrrole-2-carboxylic acid) particles synthesized by enzymatic catalysis. RSC Adv 5:105475–105483

    Article  CAS  Google Scholar 

  12. Lourenço N, Österreicher N, Vidinha P, Barreiros S, Afonso C, Cabral J, Fonseca L (2011) Effect of gelatin-ionic liquid functional polymers on glucose oxidase and horseradish peroxidase kinetics. React Funct Polym 71:489–495

    Article  Google Scholar 

  13. Pakalapati H, Arumugasamy S, Khalid M (2019) Comparison of response surface methodology and feedforward neural network modeling for polycaprolactone synthesis using enzymatic polymerization. Biocatal Agric Biotechnol 18:101046

    Article  Google Scholar 

  14. Al-Bagmi M, Khan M, Ismael M, Al-Senaidy A, Bacha A, Husain F, Alamery S (2019) An efficient methodology for the purification of date palm peroxidase: stability comparison with horseradish peroxidase (HRP). Saudi J Biol Sci 26:301–307

    Article  Google Scholar 

  15. Das D, Pham H, Lee S, Noh I (2019) Fabrication of alginate-based stimuli-responsive, non-cytotoxic, terpolymeric semi-IPN hydrogel as a carrier for controlled release of bovine albumin serum and 5-amino salicylic acid. Mater Sci Eng C 98:42–53

    Article  CAS  Google Scholar 

  16. Kaya İ, Kolcu F (2018) Polymerization of chrysoidine with chemical and enzymatic oxidative preference: synthesis, characterization, and spectroscopic study. Polym Adv Technol 29:2515–2528

    Article  CAS  Google Scholar 

  17. Li X, Huang M, Chen R, Jin Y, Yang Y (2001) Preparation and characterization of poly(p-phenylenediamine-co-xylidine). J Appl Polym Sci 81:3107–3116

    Article  CAS  Google Scholar 

  18. Temizkan K, Kaya İ (2020) Fluorescence quantum yields and chromatic properties of poly(azomethine)s containing pyridine ring. Mater Sci Eng B 252:114483

    Article  CAS  Google Scholar 

  19. Markam R, Bajpai A (2020) Functionalization of ginger derived nanoparticles with chitosan to design drug delivery system for controlled release of 5-amino salicylic acid (5-ASA) in treatment of inflammatory bowel diseases: an in vitro study. React Funct Polym 149:104520

    Article  CAS  Google Scholar 

  20. Markam R, Bajpai J, Bajpai A (2019) Synthesis of ginger derived nanocarriers (GDNC) and study of in vitro release of 5-amino salicylic acid (5-ASA) as an anti-inflammatory drug. J Drug Deliv Sci Technol 50:355–364

    Article  CAS  Google Scholar 

  21. Kolcu F, Kaya İ (2020) A study of the chemical and the enzyme-catalyzed oxidative polymerization of aromatic diamine bearing chlor substituents, pursuant to structural, thermal and photophysical properties. Eur Polym J 133:109767

    Article  CAS  Google Scholar 

  22. Kaya İ, Yağmur HK (2020) Synthesis and characterization of poly(3,5-diaminobenzoic acid) via enzymatic and oxidative polymerization and application in methylene blue adsorption. J Mol Struct 1216:128323

    Article  CAS  Google Scholar 

  23. Iqbal M, Ashiq M (2007) Adsorption of dyes from aqueous solutions on activated charcoal. J Hazard Mater 139:57–66

    Article  CAS  Google Scholar 

  24. Fajri L, Nawi M, Sabar S, Nawawi N (2018) Preparation of immobilized activated carbon polyvinyl alcohol composite for the adsorptive removal of 2,4-dichlorophenoxyacetic acid. J Water Process Eng 25:269–277

    Article  Google Scholar 

  25. Colladet K, Nicolas M, Goris L, Lutsen L, Vanderzande D (2004) Low-band gap polymers for photovoltaic applications. Thin Solid Films 7:451–452

    Google Scholar 

  26. Cheng Y, Yang S, Hsu C (2009) Synthesis of conjugated polymers for organic solar cell applications. Chem Rev 109:5868–5923

    Article  CAS  Google Scholar 

  27. Li H, Bai J, Shi Z, Yin J (2016) Environmental friendly polymers based on Schiff-base reaction with self-healing, remolding and degradable ability. Polymer 85:106–113

    Article  CAS  Google Scholar 

  28. Yuvaraja G, Chen D, Pathak J, Long J, Subbaiah M, Wen J, Pan C (2020) Preparation of novel aminated chitosan Schiff’s base derivative for the removal of methyl orange dye from aqueous environment and its biological applications. Int J Biol Macromol 146:1100–1110

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Polymer Synthesis and Analysis Laboratory, Department of Chemistry, Çanakkale Onsekiz Mart University, 17020, Çanakkale, Turkey

    İsmet Kaya & HaticeKaraer Yağmur

  2. Faculty of Science, Department of Chemistry, Dicle University, 21400, Diyarbakır, Turkey

    HaticeKaraer Yağmur

Authors
  1. İsmet Kaya
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  2. HaticeKaraer Yağmur
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Correspondence to İsmet Kaya.

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Kaya, İ., Yağmur, H. Synthesis of poly(4-aminosalicylic acid) through enzymatic and oxidative polycondensation by H2O2 oxidant. Iran Polym J 31, 199–214 (2022). https://doi.org/10.1007/s13726-021-00990-1

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  • DOI: https://doi.org/10.1007/s13726-021-00990-1

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