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Enzymatic Synthesis of a Conducting Aniline and 2-aminophenethyl Alcohol Copolymer with Functional Groups

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Abstract

The copolymers of aniline (ANI) and 2-aminophenethyl alcohol (APA) were synthesized on a poly (2-acrylamido-2-methyl-1-propanesulfonic) acid (PAMPS) template with the fungal laccase Trametes hirsuta, which has a high redox potential, as the catalyst. Atmospheric oxygen was the oxidizing agent. The copolymer/PAMPS complexes were pseudo-soluble and were characterized by various physicochemical methods. The electrical conductivity of the copolymers depended on the initial molar ratio of the monomers. The copolymer synthesized at an APA : ANI ratio of 2 : 8 possessed the best characteristics. It is shown that the laccase/mediator system can be to oxidize the primary alcohol groups of the copolymer to reactive aldehyde groups.

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REFERENCES

  1. Mendes, P.M., Chem. Soc. Rev., 2008, vol. 37, no. 11, pp. 2512–2529.

    Article  CAS  Google Scholar 

  2. Das, T.K.;. and Prusty, S., Polymer-Plast. Tech. Eng., 2012, vol. 51, no. 14, pp. 1487–1500.

    Article  CAS  Google Scholar 

  3. Hackett, A.J., Malmstrom, J., and Travas-Sejdic, J., Prog. Polym. Sci., 2017, vol. 70, pp. 18–33.

    Article  CAS  Google Scholar 

  4. Bhadra, S., Khastgir, D., Singha, N.K., and Lee, J.H., Prog. Polym. Sci., 2009, vol. 34, no. 8, pp. 783–810.

    Article  CAS  Google Scholar 

  5. Ćirić-Marjanović, G., Synth. Met., 2013, vol. 17, pp. 1–47.

    Article  Google Scholar 

  6. Jaymand, M., Prog. Polym. Sci., 2013, vol. 38, no. 9, pp. 1287–2013.

    Article  CAS  Google Scholar 

  7. Kulkarni, M.V. and Viswanath, A.K., Eur. Polym. J., 2004, vol. 40, no. 2, pp. 379–384.

    Article  CAS  Google Scholar 

  8. Vasil'eva, I.S., Morozova, O.V., Shumakovich, G.P., Shleev, S.V., Sakharov, I.Yu., and Yaropolov, A.I., Synth. Met., 2007, vol. 157, nos. 18–20, pp. 684–689.

    Article  CAS  Google Scholar 

  9. Shumakovich, G., Kurova, V., Vasil’eva, I., Pankratov, D., Otrokhov, G., Morozova, O., and Yaropolov, A., J. Mol. Cat., 2012, vol. 77, pp. 105–110.

    Article  CAS  Google Scholar 

  10. Shumakovich, G.P., Vasil’eva, I.S., Morozova, O.V., Khomenkov, V.G., Staroverova, I.N., Budashov, I.A., Kurochkin, I.N., Boyeva, J.A., Sergeyev, V.G., and Yaropolov, A.I., J. Appl. Polym. Sci., 2010, vol. 117, no. 3, pp. 1544–1550.

    CAS  Google Scholar 

  11. Borole, D.D., Kapadi, U.R., Mahulikar, P.P., and Hundiwale, D.G., Mater. Lett., 2004, vol. 58, no. 29, pp. 3816–3822.

    Article  CAS  Google Scholar 

  12. Abbasian, M., Jaymand, M., and Bonab, S.E.S., J. App-l. Polym. Sci., 2012, vol. 125, no. S1, pp. E131–E140.

    Article  CAS  Google Scholar 

  13. Gazotti, W.A. and DePaoli, M.A., Synth. Met., 1996, vol. 80, no. 3, pp. 263–269.

    Article  CAS  Google Scholar 

  14. Gok, A., Sari, B., and Talu, M., Synth. Met., 2004, vol. 142, nos. 1–3, pp. 41–48.

    Article  CAS  Google Scholar 

  15. Waware, U.S., Rashid, M., and Summers, G.J., Polymer-Plast. Tech. Eng., 2018, vol. 57, no. 10, pp. 1015–1025.

    Article  CAS  Google Scholar 

  16. Baek, S., Ree, J.J., and Ree, M., J. Polym. Sci. Part A: Polym. Chem., 2002, vol. 40, no. 8, pp. 983–994.

    Article  CAS  Google Scholar 

  17. Fatuch, J.C., Soto-Oviedo, M.A., Avellaneda, C.O., Franco, M.F., Romao, W., De Paoli, M.A., and Nogueira, A.F., Synth. Met., 2009, vol. 159, nos. 21–22, pp. 2348–2354.

    Article  CAS  Google Scholar 

  18. Lashkenari, M.S. and Eisazadeh, H., Adv. Polym. Technol., 2014, vol. 33, no. S1, article no. 21466.

    Article  Google Scholar 

  19. Ćirić-Marjanović, G., Milojević-Rakić, M., Janošević-Ležaić, A., Luginbűhl, S., and Walde, P., Chem. Pap., 2017, vol. 71, no. 2, pp. 199–242.

    Article  Google Scholar 

  20. Xu, P., Singh, A., and Kaplan, D., Adv. Polym. Sci., 2006, vol. 194, pp. 69–94.

    Article  CAS  Google Scholar 

  21. Otrokhov, G.V., Morozova, O.V., Vasil’eva, I.S., Shumakovich, G.P., Zaitseva, E.A., Khlupova, M.E., and Yaropolov, A.I., Biochemistry (Moscow), 2013, vol. 73, no. 13, pp. 1539–1553.

    Article  Google Scholar 

  22. Streltsov, A.V., Shumakovich, G.P., Morozova, O.V., Gorbacheva, M.A., and Yaropolov, A.I., Appl. Biochem. Microbiol., 2008, vol. 44, no. 3, pp. 264–270.

    Article  CAS  Google Scholar 

  23. Streltsov, A.V., Morozova, O.V., Arkharova, N.A., Klechkovskaya, V.V., Staroverova, I.N., Shumakovich, G.P., and Yaropolov, A.I., J. Appl. Polym. Sci., 2009, vol. 114, no. 2, pp. 928–934.

    Article  CAS  Google Scholar 

  24. Yaropolov, A.I., Skorobogatko, O.V., Vartanov, S.S., and Varfolomeyev, S.D., Appl. Biochem. Biotechnol., 1994, vol. 49, no. 3, pp. 257–280.

    Article  CAS  Google Scholar 

  25. Mate, D.M. and Alcalde, M., Microb. Biotechnol., 2017, vol. 10, no. 6, pp. 1457–1467.

    Article  CAS  Google Scholar 

  26. Cannatelli, M.D. and Ragauskas, A.J., Chem. Rec., 2017, vol. 17, no. 1, pp. 122–140.

    Article  CAS  Google Scholar 

  27. Witayakran, S. and Ragauskas, A.J., Adv. Synth. Catal., 2009, vol. 351, no. 9, pp. 1187–1209.

    Article  CAS  Google Scholar 

  28. Mogharabi, M. and Faramarzi, M.A., Adv. Synth. Catal., 2014, vol. 356, no. 5, pp. 897–927.

    Article  CAS  Google Scholar 

  29. Gorshina, E.S., Rusinova, T.V., Biryukov, V.V., Morozova, O.V., Shleev, S.V., and Yaropolov, A.I., Appl. Biochem. Microbiol., 2006, vol. 42, no. 6, pp. 558–563.

    Article  CAS  Google Scholar 

  30. Yuan, G., Kuramoto, N., and Su, S., Synth. Met., 2002, vol. 129, no. 2, pp. 173–178.

    Article  CAS  Google Scholar 

  31. Haba, Y., Segal, E., Narkis, M., Titelman, G., and Siegmann, A., Synth. Met., 1999, vol. 106, no. 1, pp. 59–66.

    Article  CAS  Google Scholar 

  32. Morozova, O.V., Shumakovich, G.P., Shleev, S.V., and Yaropolov, A.I., Appl. Biochem. Microbiol., 2007, vol. 43, no. 5, pp. 523–535.

    Article  CAS  Google Scholar 

  33. Fabbrini, M., Galli, C., Gentilli, P., and Macchitella, D., Tetrahedron Lett., 2001, vol. 42, no. 43, pp. 7551–7553.

    Article  CAS  Google Scholar 

  34. Galletti, P., Pori, M., Funiciello, F., Soldati, R., Ballardini, A., and Giacomini, D., ChemSusChem, 2014, vol. 7, no. 9, pp. 2684–2689.

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The equipment of the Collective Use Center Industrial Biotechnologies of the Research Center of Biotechnology of the Russian Academy of Sciences was used in the work.

Funding

The study was carried out as part of the state task of the Bach Institute of Biochemistry of the Research Center of Biotechnology of the Russian Academy of Sciences.

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Correspondence to A. I. Yaropolov.

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The authors declare that they have no conflict of interest. This article does not contain any studies involving animals or human participants performed by any of the authors.

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Khlupova, M.E., Shumakovich, G.P., Vasil’eva, I.S. et al. Enzymatic Synthesis of a Conducting Aniline and 2-aminophenethyl Alcohol Copolymer with Functional Groups. Appl Biochem Microbiol 56, 441–445 (2020). https://doi.org/10.1134/S0003683820040080

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  • DOI: https://doi.org/10.1134/S0003683820040080

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