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Enzymatic catalysis of 2,6-dimethoxyphenol by laccases and products characterization in organic solutions

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Abstract

2,6-Dimethoxyphenol (DMP) as a substrate was widely used in determination of laccase activity. It is surprising, however, that its catalyzed oxidation products have not been completely determined until now. Studies were thus conducted on Rhus laccase (RL) and immobilized Rhus laccase (IRL)-catalyzed oxidation reactions of 2,6-dimethoxyphenol in water-organic solvent systems. These reactions proceeded well in water-(im)miscible organic solvent systems pre-saturated with water. Only one product, 3,3′,5,5′-tetramethoxy-1,1′biphenyl-4,4′-diol (TMBP), was produced by RL catalysis, and it was thoroughly characterized by FT-IR, NMR, GC-MS, etc. A simple enzymatic mechanism of this reaction is propos

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References

  1. Wan Y Y, Du Y M, Miyakoshi T. Rhus laccase catalysis and product characterization of 1,2-Dimethoxyphenol in organic solutions. Chinese Chem Lett, 2008, 19(3): 333–336

    Article  CAS  Google Scholar 

  2. Baldrian P. Fungal laccases-occurrence and properties. FEMS Microbiol Rev, 2005, 30: 215–242

    Article  Google Scholar 

  3. Wan Y Y, Du Y M. Structure and catalytic mechanism of laccases. Chemistry, 2007, 70: 662–670

    CAS  Google Scholar 

  4. Okazaki S Y, Goto M, Wariishi H, Tanaka H, Furusaki S. Characterization and catalytic property of surfactant-laccase complex in organic media. Biotechnol Progr, 2000, 16: 583–588

    Article  CAS  Google Scholar 

  5. Machonkin T E, Quintanar L, Palmer A E, Hassett R, Severance S, Kosman D J, Solomon E I. Spectroscopy and reactivity of the type 1 copper site in Fet3p from Saccharomyces cerevisiae: Correlation of structure with reactivity in the multicopper oxidases. J Am Chem Soc, 2001, 123: 5507–5517

    Article  CAS  Google Scholar 

  6. Lee S K, George S D, Antholine W E, Hedman B, Hodgson K O, Solomon E I. Nature of the intermediate formed in the reduction of O2 to H2O at the trinuclear copper cluster active site in native laccase. J Am Chem Soc, 2002, 124: 6180–6193

    Article  CAS  Google Scholar 

  7. Chen C L, Gratzl J S, Kirkman A G, Miyakoshi T. Proceedings of the 5th brazilian symposium on the chemistry of lignins and other wood components. Curitiba, PR, Brazil. 8-13, 1997, 547–556

  8. Shiba T, Xiao L, Miyakoshi T, Chen C L. Oxidation of isoeugenol and coniferyl alcohol catalyzed by laccases isolated from Rhus vernicifera stokes and Pycnoporus coccineus. J Mol Catal B: Enzym, 2000, 10: 605–615

    Article  CAS  Google Scholar 

  9. Rodakiewicz-Nowak J, Kasture S M, Dudek B, Haber J. Effect of various water-miscible solvents on enzymatic activity of fungal laccases. J Mol Catal B: Enzym, 2000, 11: 1–11

    Article  CAS  Google Scholar 

  10. Du Y M. New advance on study Chinese lacquer. Chemistry, 1986, 1–9

  11. Mayer A M, Staples R C. Laccase: new functions for an old enzyme. Phytochemistry, 2002, 60: 551–565

    Article  CAS  Google Scholar 

  12. Mustafa R, Muniglia R, Rovel G, Girardin M. Phenolic colorants obtained by enzymatic synthesis using a fungal laccase in a hydro-organic biphasic system. Food Res Int, 2005, 38: 995–1000

    Article  CAS  Google Scholar 

  13. Nicotra S, Intra A, Ottolina G, Riva S, Danieli B. Laccase-mediated oxidation of the steroid hormone 17β-estradiol in organic solvents. Tetrahedron-Asymmetr, 2004, 15: 2927–2931

    Article  CAS  Google Scholar 

  14. Wan Y Y, Du Y M, Yang F X, Xu Y, Chen R Z, Kennedy J F. Purification and characterization of hydrosoluble components from the sap of Chinese lacquer tree Rhus vernicifera. Int J Biol Macromol, 2006, 38: 232–240

    Article  CAS  Google Scholar 

  15. Wan Y Y, Lu R, Du Y M, Honda T, Miyakoshi T. Does Donglan lacquer tree belong to Rhus vernicifera species? Int J Biol Macromol, 2007, 41: 497–503

    Article  CAS  Google Scholar 

  16. Wan Y Y, Du Y M, Shi X W, Li J, Ru L, Miyakoshi T. Immobilization and characterization of Rhus laccase from Chinese Rhus vernicifera on modified chitosan. Process Biochem, 2006, 41: 1378–1382

    Article  Google Scholar 

  17. Du Y M, Zhang J M. Studies on oxidation performance and reaction product of Rhus laccase in reverse micelle. Chem J Chin Univ, 1995, 16: 715–718

    CAS  Google Scholar 

  18. Wan Y Y, Lu R, Akiyama K, Miyakoshi T, Du Y M. Enzymatic synthesis of bioactive compounds by Rhus laccase from Chinese Rhus vernicifera. Sci China Ser B: Chem, 2007, 50: 179–182

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. State Key Laboratory of Petroleum Resources and Prospecting, Faculty of Natural Resources and Information Technology, China University of Petroleum, Beijing, 102249, China

    YunYang Wan

  2. Department of Industrial Chemistry, Meiji University, Higashi-mita, Tama-ku, Kawasaki, 214, Japan

    YunYang Wan & Tetsuo Miyakoshi

  3. School of Resource and Environment Science, Wuhan University, Wuhan, 430079, China

    YuMin Du

Authors
  1. YunYang Wan
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  2. YuMin Du
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  3. Tetsuo Miyakoshi
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Correspondence to YunYang Wan.

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This paper is dedicated to professor Du YuMin on the occasion of his 70th birthday

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Wan, Y., Du, Y. & Miyakoshi, T. Enzymatic catalysis of 2,6-dimethoxyphenol by laccases and products characterization in organic solutions. Sci. China Ser. B-Chem. 51, 669–676 (2008). https://doi.org/10.1007/s11426-008-0071-y

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  • DOI: https://doi.org/10.1007/s11426-008-0071-y

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