JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 61 No 3 (2016): Journal of the Chilean Chemical Society
Original Research Papers

LACASSE CATALYZED-SYNTHESIS OF 4,4’-BIPHENYLDIAMINE FROM P-CHLOROANILINE. EVALUATION OF ANTIFUNGAL AND ANTIOXIDANT ACTIVITIES

Ana M. Campos
Facultad de Química y Biología, Universidad de Santiago de Chile
Leonora Mendoza
Facultad de Química y Biología, Universidad de Santiago de Chile
Juan Vásquez
Facultad de Química y Biología, Universidad de Santiago de Chile
Ricardo Melo
Facultad de Química y Biología, Universidad de Santiago de Chile
Jennifer Salas
Facultad de Química y Biología, Universidad de Santiago de Chile
Milena Cotoras
Facultad de Química y Biología, Universidad de Santiago de Chile
Published May 23, 2017
Keywords
  • P-chloroaniline,
  • 4,
  • 4’-Biphenyldiamine,
  • Laccase,
  • Antioxidant activity,
  • Antifungal activity
  • ...More
    Less
How to Cite
Campos, A. M., Mendoza, L., Vásquez, J., Melo, R., Salas, J., & Cotoras, M. (2017). LACASSE CATALYZED-SYNTHESIS OF 4,4’-BIPHENYLDIAMINE FROM P-CHLOROANILINE. EVALUATION OF ANTIFUNGAL AND ANTIOXIDANT ACTIVITIES. Journal of the Chilean Chemical Society, 61(3). Retrieved from https://jcchems.com/index.php/JCCHEMS/article/view/67

Abstract

Laccase is a copper-containing oxidase that catalyzes reduction of molecular oxygen to water and the oxidation of a phenolic compound. In this paper, laccase was utilized to synthesize 4,4’-Biphenyldiamine using p-chloroaniline as substrate by means of a coupling reaction. The synthesized compound, 4,4’-Biphenyldiamine, presented low antifungal activity against the phytopathogenic fungus Botrytis cinerea, however the antioxidant ability, measurement by ORAC-PGR method, was higher than substrate.

This work corresponds to the first report of synthesis 4,4’-Biphenyldiamine, from p-chloroaniline in a lacasse-catalyzed reaction. 

References

  1. O.V. Morozova, G.P. Shumakovich, M.A. Gorbacheva, S.V. Shleev, A. Yaropolov, Biochem.72, 1136, (2007).
  2. T. Kudanga, G.S. Nyanhongo, G.M. Guebitz, S. Burton, Enz. Microbial Tech. 48, 195, (2011).
  3. U. Jonas, E. Hammer, E.T.K. Haupt, F. Schauer, Arch. Microbiol.174,393 (2000).
  4. T. Shiba, L. Xiao, T. Miyakoshi, C. Chen, J. Mol. Catal. B. Enzym, 10(6), 7 (2000).
  5. O.E. Adelakun,T. Kudanga,A. Parker,I.R. Green, M. le Roes-Hill, S.G Burton,. J. Mol. Catal. B Enzym.74, 29, (2012).
  6. S. Witayakran,A.J. Ragauskas, Adv. Synth. Catal.351, 1187, (2009).
  7. T.H.J. Niedermeyer, A. Mikolasch, M. Lalk, J. Org. Chem.70, 2002 (2005).
  8. V. Ibrahim, N. Volkova,S.H. Pyo, G. Mamo, R. Hatti-Kaul, Acid. J. Mol. Catal. B Enzym.97, 45, (2013).
  9. Mikolasch, T.H.J. Niedermeyer, M. Lalk, S. Witt, S. Seefeldt, E. Hammer, F. Schauer, M. Gesell, S. Hessel, W.D. Jülich, et al. Chem. Pharm. Bull. (Tokyo).54, 632, (2006).
  10. Mikolasch, S. Hessel, M.G. Salazar, H. Neumann, K. Manda, D. Gordes, E. Schmidt, K. Thurow, E. Hammer, U. Lindequist, et al. Chem. Pharm. Bull.56, 781, (2008).
  11. Mikolasch, T.H.J. Niedermeyer, M. Lalk, S. Witt, S. Seefeldt, E. Hammer, F. Schauer, M. Gesell Salazar, S. Hessel, W.D. Jülich, et al. Chem. Pharm. Bull. (Tokyo).55, 412, (2007).
  12. K.W. Wellington, N.I. Kolesnikova, Bioorg. Med. Chem.20, 4472, (2012).
  13. J.R. Jeon, Y.S. Chang, Trends in Biotechnology, 31(6), 335, (2013).
  14. G. Shumakovich, V. Kurova, I. Vasil’eva, D. Pankratov, G. Otrokhov, O. Morozova, A. Yaropolov, J. Mol. Catal. B. Enzym. 77,105, (2012).
  15. M. Kurisawa, J. Chung, H. Uyama, S. Kobayashi, Biomacromolecules, 4, 1394 (2003).
  16. M.G. Hossain, M.D. González, G.R. Lozano, T. Tzanov, J. Biotech. 141, 58 (2009).
  17. A.A.Leontievsky, N.M. Myasoedova, B.P. Baskonov, L.A. Golovleva, C.S. Evans. Biodegradation 11(5), 331, (2000).
  18. G. Dawel, M. Kastner, J. Michels, W. Poppitz, W. Gunther, W. Fritsche, Applied Environ. Microbiol. 63(7), 2560, (1997).
  19. J. F. Osma, J. Toca-Herrera, S. Rodriguez-Couto, Dyes & Pigments, 75, 32, (2007).
  20. Cantarelli, Vinid’Italia, 3, 87, (1986).
  21. M. Božiča, J. Štrancarb, V. Kokola, Reac. Func. Polymers 73(10), 1377, (2013).
  22. Aljawish, I. Chevalot J. Jasniewski, A.M. Revol-Junelles, J. Scher, J. Muniglia, Food Chem. 161, 279, (2014).
  23. P. Leroux in the Chemical Control of Botrytis and Its Resistance to Chemical Fungicides. In Botrytis: Biology, pathology and control; Y. Elad, B. Williamson, P. Tudzynski, N. Delen, N., Eds.; Springer: Dordrecht, Netherlands, 2007; pp. 195–217.
  24. G. Muñoz, P. Hinrichsen,Y. Brygoo, T. Giraud, Mycol. Res.106, 594, (2002).
  25. A.C. Poblete, B. E. López-Alarcón, C. Lissi, A.M. Campos, J. Chil. Chem. Soc. 54(2), 14, (2009).
  26. R. Silverstein, F. Webster, D. Kiemle. Spectrometric identification of organic compounds, John Wiley & Sons, (2005).
  27. Hinks, H.S. Freemana, M. Nakpathoma, J. Sokolowskab, (2000). Dyes and Pigments, 44(3), 199, (2000).
  28. T. Hoff, S.Y. Liu, J.M. Bollag, App. Environ. Microbiol. 49 (5), 1044, (1985).
  29. W.G. Levine, W. G. in the Laccase, a review, In J.J. Peisach, D. Aisen, and W.E. Blumberg, ed. The biochemistry of copper. Academic Press, Inc., New York, (1966); p. 371-387.
  30. K.E. Simmonds, R.D. Minard, J.M. Bollag, Environ. Sci. Technol. 27, 999, (1987).
  31. Longoria, H. Hub, R. Tinoco-Valencia, R. Vásquez-Duhalt, TIP Revista Especializada en Ciencias Químico-Biológicas, 11(2), 73, (2008).
  32. L. Mendoza, M. Cotoras, M. Vivanco, B. Matsuhiro, S. Torres, M.J. Aguirre, J. Chil. Chem. Soc. 58(2), 1725, (2013).
  33. M. Adrian, P. Jeandet, J. Veneau, L. Weston, R. Besis, J. Chem. Ecol. 23, 1689, (1997).
  34. F. Caruso, L. Mendoza, P. Castro, M. Cotoras, M.J. Aguirre, B. Matsuhiro, M. Isaacs, M. Rossi, A. Viglianti, R. Antonieletti, PLOS-ONE 6(10), e25421, (2011).
  35. A.Schouten, L. Wagemakers, F.L. Stefanato, R.M. Van der Kaaij, J.A.L van Kan, Mol. Microbiol. 43, 883, (2002).

Copyright @2019 | Designed by: Open Journal Systems Chile Logo Open Journal Systems Chile Support OJS, training, DOI, Indexing, Hosting OJS

Code under GNU license: OJS PKP