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.
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Neilson, A.H. and Allard, A-S., Environmental Degradation and Transformation of Organic Chemicals, New York: CRC Press, 2008.
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.
Nakatani, N., Hitomi, Y., and Sakaki, S., J. Phys. Chem. B, 2011, vol. 115, pp. 4781–4789.
Nakatani, N., Nakao, Y., and Sato, H., J. Phys. Chem. B, 2009, vol. 113, pp. 4826–4836.
Abu-Omar, M.M., Loaiza, A., and Hontzeas, N., Chem. Rev., 2005, vol. 105, no. 6, pp. 2227–2252.
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.
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.
Natarajan, M.R. and Oriel, P., Biotechnol. Progr., 1992, vol. 8, pp. 78–80.
Orville, A.M., Elango, N., Lipscomb, J.D., and Ohlendorf, D., Biochemistry, 1997, vol. 36, pp. 10039–10051.
Broderick, J.B. and O’Halloran, T.V., Biochemistry, 1991, vol. 30, pp. 7349–7358.
Kovaleva, E.G., Neibergall, M.B., Chakrabarty, S., and Lipscomb, J.D., Acc. Chem. Res., 2007, vol. 40, pp. 475–483.
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.
Mendel, S., Arndt, A., and Bugg, T.D.H., Biochemistry, 2004, vol. 43, pp. 13390–13396.
Vasil’ev, D.A., Viktorov, D.A., and Bogdanov, I.I., Estestv. Tekhn. Nauki, 2011, no. 2, pp. 79–82.
Li, X., Wang, X., Chen, D., and Chen, Sh., Functional Foods in Health and Disease, 2011, vol. 7, no. 1, pp. 232–244.
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Original Russian Text © A.S. Lebedev, V.Yu. Orlov, 2014, published in Prikladnaya Biokhimiya i Mikrobiologiya, 2014, Vol. 50, No. 4, pp. 414–421.
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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
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DOI: https://doi.org/10.1134/S0003683814040073


