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Oxidative biotransformation of thioanisole by Rhodococcus rhodochrous IEGM 66 cells

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Abstract

Comparative study of sulfoxidation activity of free and immobilized Rhodococcus rhodochrous IEGM 66 cells was performed. Free Rhodococcus cells (in the presence of 0.1 vol % n-hexadecane) displayed maximal oxidative activity towards thioanisole (0.5 g/l), a prochiral organic sulfide, added after 48-h cultivation of bacterial cells. Higher sulfide concentrations inhibited sulfoxidation activity of Rhodococcus. Use of immobilized cells allowed the 2-day preparatory stage to be omitted and a complete thioanisole bioconversion to be achieved in 24 h in the case that biocatalyst and 0.5 g/l thioanisole were added simultaneously. The biocatalyst immobilized on gel provides for complete thioanisole transformation into (S)-thioanisole sulfoxide (optical purity of 82.1%) at high (1.0–1.5 g/l) concentrations of sulfide substrate.

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References

  1. Al’fonsov, V.A., Belen’kii, L.I., and Vlasova, N.N., Poluchenie i svoistva organicheskikh soedinenii sery (Obtaining and Properties of Organic Sulfuric Compounds), Belen’kii, L.I., Ed., Moscow: Khimiya, 1998.

    Google Scholar 

  2. Fernandez, I. and Khiar, N., Chem. Rev., 2003, vol. 103, no.9, pp. 3651–3705.

    Article  CAS  PubMed  Google Scholar 

  3. Cotton, H., Elebring, T., Larsson, M., Li, L., Sorensen, H., and von Unge, S., Tetrahedron: Asymmetry, 2000, vol. 11, no.18, pp. 3819–3825.

    Article  CAS  Google Scholar 

  4. Andersson, T., Hassan-Alin, M., Hasselgren, G., Rhss, K., and Weidolf, L., Clin. Pharmacokinet., 2001, vol. 40, no.6, pp. 411–426.

    Article  CAS  PubMed  Google Scholar 

  5. Carreno, M.C., Chem. Rev., 1995, vol. 95, no.6, pp. 1717–1760.

    Article  CAS  Google Scholar 

  6. Volcho, K.P., Salakhutdinov, N.F., and Tolstikov, A.G., Zh. Org. Khim., 2003, vol. 39, no.11, pp. 1607–1622.

    Google Scholar 

  7. Holland, H.L., Chem. Rev., 1988, vol. 88, no.3, pp. 473–485.

    Article  CAS  Google Scholar 

  8. Holland, H.L., Nat. Prod. Rep., 2001, vol. 18, no.2, pp. 171–181.

    Article  CAS  PubMed  Google Scholar 

  9. Tolstikov, A.G., Grishko, V.V., and Ivshina, I.B., Sovremennye problemy asimmetricheskogo sinteza (Modern Problems of Asymmetric Synthesis), Tolstikov, A.G., Ed., Yekaterinburg: Ural. Otd. Ross. Akad. Nauk, 2003.

    Google Scholar 

  10. Ohta, H., Okamoto, Y., and Tsuchihashi, G., Chem. Lett., 1984, vol. 13, no.2, pp. 205–208.

    Article  Google Scholar 

  11. Ohta, H., Okamoto, Y., and Tsuchihashi, G., Agric. Biol. Chem., 1985, vol. 49, no.3, pp. 671–676.

    CAS  Google Scholar 

  12. Holland, H.L., Brown, F.M., Kerridge, A., Pienkos, P., and Arensdor, J., J. Mol. Catal. B: Enzymatic, 2003, vol. 22, nos.3–4, pp. 219–223.

    Article  CAS  Google Scholar 

  13. French, J.B., Holland, G., Holland, H.L., and Gordon, H.L., J. Mol. Catal. B: Enzymatic, 2004, vol. 31, nos.4–6, pp. 87–96.

    Article  CAS  Google Scholar 

  14. Grishko, V.V., Ivshina, I.B., and Tolstikov, A.G., Biotekhnologiya, 2004, no.5, pp. 49–56.

  15. Grishko, V.V., Kuyukina, M.S., Ivshina, I.B., and Tolstikov, A.G., in Tekhnicheskaya khimiya. Dostizheniya i perspektivy. Trudy Vseros. konf (Technical Chemistry: Advances and Prospects, Proc. All-Russ. Conf.), Perm: OOO TPS Garmoniya, 2006, vol. 1, pp. 73–80.

    Google Scholar 

  16. Katalog shtammov Regional’noi profilirovannoi kollektsii alkanotrofnykh mikroorganizmov (Catalogue of Strains of Regional Specialized Collection of Alcanotrophic Microorganisms), Ivshin, I.B., Ed., Moscow: Nauka, 1994.

    Google Scholar 

  17. Sojo, M., Bru, R., Lopez-Molina, D., Garcia-Carmona, F., and Arguelles, J.C., Appl. Microbiol. Biotechnol., 1997, vol. 47, no.5, pp. 583–589.

    Article  CAS  PubMed  Google Scholar 

  18. Lozinskii, V.I., Usp. Khim., 1998, vol. 67, no.7, pp. 641–652.

    Google Scholar 

  19. Kuyukina, M.S., Ivshina, I.B., Gavrin, A.Yu., Podorozhko, E.A., Lozinsky, V.I., Jeffree, C.E., and Philp, J.C., J. Microbiol. Methods, 2006, vol. 65, no.3, pp. 596–603.

    Article  CAS  PubMed  Google Scholar 

  20. Holland, H.L., Poddar, S., and Tripet, B., J. Ind. Microbiol., 1992, vol. 10, nos.3–4, pp. 195–197.

    Article  CAS  PubMed  Google Scholar 

  21. Porto, A.L.M., Cassiola, F., Dias, S.L.P., Joekes, I., Gushikem, Y., Rodrigues, J.A.R., Moran, P.J.S., Manfio, G.P., and Marsaioli, A.J., J. Mol. Catal. B: Enzymatic, 2002, vols. 19–20, pp. 327–334.

    Article  Google Scholar 

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Authors and Affiliations

  1. Institute of Ecology and Genetics of Microorganisms, Ural Division, Russian Academy of Sciences, Perm, 614081, Russia

    A. A. El’kin & I. B. Ivshina

  2. Institute of Technical Chemistry, Ural Division, Russian Academy of Sciences, Perm, 614081, Russia

    V. V. Grishko

Authors
  1. A. A. El’kin
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  2. V. V. Grishko
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  3. I. B. Ivshina
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Correspondence to I. B. Ivshina.

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Original Russian Text © A.A. El’kin, V.V. Grishko, I.B. Ivshina, 2010, published in Prikladnaya Biokhimiya i Mikrobiologiya, 2010, Vol. 46, No. 6, pp. 637–643.

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El’kin, A.A., Grishko, V.V. & Ivshina, I.B. Oxidative biotransformation of thioanisole by Rhodococcus rhodochrous IEGM 66 cells. Appl Biochem Microbiol 46, 586–591 (2010). https://doi.org/10.1134/S0003683810060050

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