Applied Biochemistry and Microbiology

, Volume 53, Issue 2, pp 187–193 | Cite as

Novel biocatalyst for productions of S-(-)-2-[6-benzyloxy -2,5,7,8-tetramethylchroman -2-yl] ethanol—precursor of natural α-tocols

  • N. I. Petukhova
  • I. I. Kon’shina
  • A. Yu. Spivak
  • V. N. Odinokov
  • V. V. Zorin
Article
  • 25 Downloads

Abstract

A novel promising strain of actinobacteria Rhodococcus sp. 77-32 was identified. Its acetonetreated biomass the could be used as a biocatalyst for production of S-(-)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl] ethanol (S-BCE), a precursor of natural α-tocols. It was established that a reaction of enantioselective hydrolysis of racemic (±)-2-(2-acetoxyethyl)-6-benzyloxy-2,5,7,8-tetramethylchroman (BCEA) occurred in the phosphate buffer–acetone system, resulting in enrichment of the residual substrate by S-enantiomer (S-(+)-2-(2-acetoxyethyl)-6-benzyloxy-2,5,7,8-tetramethylchroman, S-BCEA). It was shown that the hydrolysis was accompanied by stereoinversion of the formed product, R-(+)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl] ethanol (R-BCE), into the S-BCE. The transformation conditions (acetone content, acidity, temperature, reaction duration) were optimized, providing simultaneous production of optically pure S-BCE and S-BCEA with an almost quantitative yield.

Keywords

microorganisms biocatalysts enantioselective biocatalysis tocopherols tocotrienols 

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References

  1. 1.
    Bezborodov, A.M. and Zagustina, N.A., Appl. Biochem. Microbiol., 2014, vol. 50, no. 4, pp. 313–337.CrossRefGoogle Scholar
  2. 2.
    Faber, K., Biotransformations in Organic Chemistry, Berlin Springer, 2011.CrossRefGoogle Scholar
  3. 3.
    Busto, E., Gotor-Fernandez, V., and Gotor, V., Chem. Soc. Rev., 2010, vol. 39, pp. 4504–4523.CrossRefPubMedGoogle Scholar
  4. 4.
    Gotor-Fernandez, V. and Vicente, G., Industrial Enzymes, Structure, Function and Applications, Polaina, J. and MacCabe, A.P., Eds., Weinheim Springer, 2007.Google Scholar
  5. 5.
    Zorin, V.V., Petukhova, N.I., and Khalimova, L.Kh., in Panorama sovremennoi khimii Rossii. Sovremennyi organicheskii sintez: Sb. obzornykh statei (Panorama of Modern Russian Chemistry. Modern Organic Synthesis: Collection of Review Articles), Moscow: Khimiya, 2003, pp. 439–462.Google Scholar
  6. 6.
    Bornscheuer, U.T., FEMS Microbiol. Rev., 2002, vol. 26, pp. 73–81.CrossRefPubMedGoogle Scholar
  7. 7.
    Santaniello, E., Ferraboschi, P., Grisenti, P., and Manzocchi, A., Chem. Rev., 1992, vol. 92, no. 5, pp. 1071–1140.CrossRefGoogle Scholar
  8. 8.
    Schuurmann, J., Quehl, P., Festel, G., and Jose, J., Appl. Microbiol. Biotechnol., 2014, vol. 98, pp. 8031–8046.CrossRefPubMedGoogle Scholar
  9. 9.
    Milner, S.E. and Maguire, A.R., Arkivoc, 2012 (i), pp. 321–382.Google Scholar
  10. 10.
    Zorin, V.V. and Petukhova, N.I., in Panorama sovremennoi khimii. Uspekhi organicheskogo kataliza i khimii geterotsiklov (Panorama of Modern Chemistry. Advances in Organic Catalysis and Heterocyclic Chemistry), Moscow: Khimiya, 2006, pp. 280–305.Google Scholar
  11. 11.
    Mubarakov, A.I., Khabibullina, I.I., Petukhova, N.I., and Zorin, V.V., Bash. Khim. Zh., 2003, vol. 10, no. 1, pp. 56–57.Google Scholar
  12. 12.
    Bezborodov, A.M. and Zagustina, N.A., Appl. Biochem. Microbiol., 2016, vol. 52, no. 3, pp. 237–249.CrossRefGoogle Scholar
  13. 13.
    Patel, R.N., Biomolecules, 2013, vol. 3, pp. 741–777.CrossRefPubMedPubMedCentralGoogle Scholar
  14. 14.
    Shakirov, A.N., Sharaeva, A.A., Petukhova, N.I., Shakhmaev, R.N., and Zorin, V.V., Bash. Khim. Zh., 2013, vol. 20, no. 2, pp. 93–95.Google Scholar
  15. 15.
    Patel, R.N., Coordination Chem. Rev., 2008, vol. 252, nos. 5–7, pp. 659–701.CrossRefGoogle Scholar
  16. 16.
    Kon’shina, I.I., Kon’shin, P.S., Petukhova, N.I., Vershinin, S.S., and Zorin, V.V., Bash. Khim. Zh, 2008, vol. 15, no. 1, pp. 14–15.Google Scholar
  17. 17.
    Ghanem, A., Tetrahedron, 2007, vol. 63, pp. 1721–1754.CrossRefGoogle Scholar
  18. 18.
    Patel, R.N., Food Technol. Biotechnol., 2004, vol. 42, no. 4, pp. 305–325.Google Scholar
  19. 19.
    Konovalov, A.A., Petukhova, N.I., and Zorin, V.V., Bash. Khim. Zh., 2003, vol. 10, no. 1, pp. 64–65.Google Scholar
  20. 20.
    Patel, R.N., Enzyme Microb. Technol., 2002, vol. 31, no. 6, pp. 804–826.CrossRefGoogle Scholar
  21. 21.
    Konovalov, A.A., Petukhova, N.I., and Zorin, V.V., Bash. Khim. Zh., 2000, vol. 7, no. 5, pp. 49–50.Google Scholar
  22. 22.
    Mori, K., Tetrahedron, 1989, vol. 45, no. 11, pp. 3233–3298.CrossRefGoogle Scholar
  23. 23.
    Odinokov, V.N., Spivak, A.Yu., Emel’yanova, G.A., Gamalevich, G.D., and Serebryakov, E.P., Izv. AN SSSR, Ser. Khim., 2001, no. 11, pp. 1–8.Google Scholar
  24. 24.
    Spivak, A.Yu., Shafikov, R.V., and Odinokov, V.N., Arkivoc, 2011 (viii), pp. 67–75.Google Scholar
  25. 25.
    Hyatt, J.A. and Skelton, C., Tetrahedron: Asymmetry, 1997, vol. 8, no. 4, pp. 523–526.CrossRefGoogle Scholar
  26. 26.
    Mizuguchi, E., Suzuki, T., and Achiwa, K., Synlett, 1994, no. 11, pp. 929–930.CrossRefGoogle Scholar
  27. 27.
    Khabibullina, I.I., Petukhova, N.I., Odinokov, V.N., Spivak, A.Yu., Mallyabaeva, M.I., and Zorin, V.V., Bash. Khim. Zh, 2004, vol. 11, no. 1, pp. 51–53.Google Scholar
  28. 28.
    Khabibullina, I.I., Petukhova, N.I., Abdul’manov, D.A., Spivak, A.Yu., Odinokov, V.N., and Zorin, V.V., Bash. Khim. Zh., 2005, vol. 12, no. 1, pp. 5–6.Google Scholar
  29. 29.
    Fujita, Y., Shiono, M., Ejiri, K., and Saita, K., Chem. Lett., 1985, pp. 1399–1400.Google Scholar
  30. 30.
    Li, X., Huang, S., Xu, L., and Yan, Y., Sci. World J., 2013, vol. 2013.Google Scholar
  31. 31.
    Secundo, F. and Carrea, G., J. Mol. Catal. B: Enzymatic, 2002, vol. 19-20, pp. 93–102.CrossRefGoogle Scholar
  32. 32.
    Overbeeke, P.L.A., Jongejan, J.A., and Heijnen, J.J., Biotechnol. Bioengenering, 2000, vol. 70, no. 3, pp. 278–290.CrossRefGoogle Scholar
  33. 33.
    Cernia, E., Palocci, C., and Soro, S., Chem. Physics Lipids, 1998, vol. 93, pp. 157–168.CrossRefGoogle Scholar
  34. 34.
    Shen, H.C., Tetrahedron, 2009, vol. 65, pp. 3931–3952.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Inc. 2017

Authors and Affiliations

  • N. I. Petukhova
    • 1
  • I. I. Kon’shina
    • 1
  • A. Yu. Spivak
    • 2
  • V. N. Odinokov
    • 2
  • V. V. Zorin
    • 1
  1. 1.Ufa State Petroleum Technologcal UniversityUfaRussia
  2. 2.Institure of Petrleum Chemistry and CatalysisRussian Academy of SciencesUfaRussia

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