Skip to main content
Log in

Analysis of functionalized arenes degradation pathways in model water-organic media

  • Published:
Applied Biochemistry and Microbiology Aims and scope Submit manuscript

Abstract

The degradation of functionalized arenes exposed to a mixed culture of chemoorganoaeroheterotrophic microorganisms has been shown to predominantly occur through oxidative intradiol decyclization of the aromatic ring. The spatial structure of the catalytic center of intradiol dioxygenase and its complexes with catechol and protocatechuic acid has been characterized using quantum chemical modeling procedures. The dependence of the total energy of the enzyme-substrate complex on the length of the bond between the iron atom and the hydroxyl group of the substrate (Fe-4-OH and Fe-1-OH) before and after the separation of water and a tyrosine residue (Tyr) from the catalytic center has been demonstrated for the first time.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+
from $39.99 /Month
  • Starting from 10 chapters or articles per month
  • Access and download chapters and articles from more than 300k books and 2,500 journals
  • Cancel anytime
View plans

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Explore related subjects

Discover the latest articles and news from researchers in related subjects, suggested using machine learning.

References

  1. Neilson, A.H. and Allard, A-S., Environmental Degradation and Transformation of Organic Chemicals, New York: CRC Press, 2008.

    Google Scholar 

  2. Ruzzini, A.C., Ghosh, S., Horsman, G.P., Foster, L.J., Bolin, J.T., and Eltis, L.D., J. Am. Chem. Soc., 2012, vol. 134, pp. 4615–4624.

    Article  CAS  PubMed  Google Scholar 

  3. Nakatani, N., Hitomi, Y., and Sakaki, S., J. Phys. Chem. B, 2011, vol. 115, pp. 4781–4789.

    Article  CAS  PubMed  Google Scholar 

  4. Nakatani, N., Nakao, Y., and Sato, H., J. Phys. Chem. B, 2009, vol. 113, pp. 4826–4836.

    Article  CAS  PubMed  Google Scholar 

  5. Abu-Omar, M.M., Loaiza, A., and Hontzeas, N., Chem. Rev., 2005, vol. 105, no. 6, pp. 2227–2252.

    Article  CAS  PubMed  Google Scholar 

  6. Pau, M.Y.M., Davis, M.I., Orville, A.M., Lipscomb, J.D., and Solomon, E.I., J. Am. Chem. Soc., 2007, vol. 129, no. 7, pp. 1944–1958.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  7. Chari, R.V.J., Whitman, C.P., Kozarich, J.W., Ngai, Ka-L., and Ornston, L.N., J. Am. Chem. Soc., 1987, vol. 109, no. 18, pp. 5514–5519.

    Article  CAS  Google Scholar 

  8. Natarajan, M.R. and Oriel, P., Biotechnol. Progr., 1992, vol. 8, pp. 78–80.

    Article  CAS  Google Scholar 

  9. Orville, A.M., Elango, N., Lipscomb, J.D., and Ohlendorf, D., Biochemistry, 1997, vol. 36, pp. 10039–10051.

    Article  CAS  PubMed  Google Scholar 

  10. Broderick, J.B. and O’Halloran, T.V., Biochemistry, 1991, vol. 30, pp. 7349–7358.

    Article  CAS  PubMed  Google Scholar 

  11. Kovaleva, E.G., Neibergall, M.B., Chakrabarty, S., and Lipscomb, J.D., Acc. Chem. Res., 2007, vol. 40, pp. 475–483.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  12. Horsman, G.P., Jirasek, A., Vaillancourt, F.H., Barbosa, Ch.J., Jarzecki, A.A., Xu, Ch., Mekmouche, Y., Spiro, Th.G., Lipscomb, J.D., Blades, M.W., Turner, R.F.B., and Eltis, L.D., J. Am. Chem. Soc., 2005, vol. 127, pp. 16882–16891.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  13. Mendel, S., Arndt, A., and Bugg, T.D.H., Biochemistry, 2004, vol. 43, pp. 13390–13396.

    Article  CAS  PubMed  Google Scholar 

  14. Vasil’ev, D.A., Viktorov, D.A., and Bogdanov, I.I., Estestv. Tekhn. Nauki, 2011, no. 2, pp. 79–82.

    Google Scholar 

  15. Li, X., Wang, X., Chen, D., and Chen, Sh., Functional Foods in Health and Disease, 2011, vol. 7, no. 1, pp. 232–244.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. S. Lebedev.

Additional information

Original Russian Text © A.S. Lebedev, V.Yu. Orlov, 2014, published in Prikladnaya Biokhimiya i Mikrobiologiya, 2014, Vol. 50, No. 4, pp. 414–421.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lebedev, A.S., Orlov, V.Y. Analysis of functionalized arenes degradation pathways in model water-organic media. Appl Biochem Microbiol 50, 374–380 (2014). https://doi.org/10.1134/S0003683814040073

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0003683814040073

Keywords