Skip to main content
SpringerLink
Log in

Asymmetric Bioreduction of 4-Chloroacetophenone Catalyzed by Daucus carota Cells in Water and Organic Solvents

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Enantioselective reduction of 1-(4-chlorophenyl)ethanone catalyzed by D. carota cells in water, organic solvents, and binary systems has been studied. We have found conditions that make it possible to obtain (S)-(–)-1-(4-chlorophenyl)ethanol by bioreduction of 1-(4-chlorophenyl)ethanone in water in the presence of an available biocatalyst D. carota and ethanol (3%) with a yield 63% (98% ee), in the presence of isopropanol (3%) with a yield of 66% (98% ee) or in the presence of glucose—with a yield of 50% (99% ee). The rate of reduction of the initial ketone by D. carota cells in the water : isooctane, water:acetonitrile, water : 1,4-dioxane system is significantly lower than in the case of a similar reduction in an aqueous medium.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme

Similar content being viewed by others

REFERENCES

  1. Suga, T., Hirata, T., and Lee, Y.S., Chem. Lett., 1982, vol. 11, no. 10, p. 1595. https://doi.org/10.1246/cl.1982.1595

    Article  Google Scholar 

  2. Ishihara, K., Hamada, H., Hirata, T., and Nakajima, N., J. Mol. Catal. B: Enzym., 2003, vol. 23, p. 145.

    Article  CAS  Google Scholar 

  3. Pawlowicz, P. and Siewinski, A., Phytochemistry, 1987, vol. 26, p. 1001.

    Article  CAS  Google Scholar 

  4. Patel, R., McNamee, C.G., Banerjee, A., Howell, J.M., Robison, R.S., and Szarka, L.J., Enzyme Microb. Technol., 1992, vol. 14, p. 731.

    Article  CAS  Google Scholar 

  5. Medson, C., Smallridge, A.J., and Trewhella, M.A., Tetrahedron: Asymmetry, 1997, vol. 8, p.1049.

    Article  CAS  Google Scholar 

  6. Hamada, H., Miura, T., Kumobayashi, H., Matsuda, T., Harada, T., and Nakamura, K., Biotechnol. Lett., 2001, vol. 23, p. 1603.

    Article  CAS  Google Scholar 

  7. Chanysheva, A.R., Privalov, N.V., and Zorin, V.V., Russ. J. Gen. Chem., 2020, vol. 90, p. 2542.

    Article  CAS  Google Scholar 

  8. Ishihara, K., Yamaguchi, H., Hamada, H., Nakajima, N., and Nakamura, K., J. Mol. Catal. B: Enzym., 2000, vol. 10, p. 429.

    Article  CAS  Google Scholar 

  9. Majewska, E. and Mironowicz, A., Tetrahedron Lett., 2013, vol. 54, no. 47, p. 6331.

    Article  CAS  Google Scholar 

  10. Villa, R. and Molinari, F., J. Nat. Prod., 2008, vol. 71, p. 693.

    Article  CAS  PubMed  Google Scholar 

  11. Andrade, L.H., Utsunomiya, R.S., Omori, A.T., Porto, A.L., and Comasseto, J.V., J. Mol. Catal. B: Enzym., 2006, vol. 38, no. 2, p. 84.

    Article  CAS  Google Scholar 

  12. Demmel, G.I., Bordón, D.L., Vázquez, A.M., Decarlini, M.F., Panero, M.D., Rossi, L.I., and Aimar, M.L., Biocatal. Biotransform., 2021. https://doi.org/10.1080/10242422.2021.1956910

  13. Chanysheva, A.R., Vorob’eva, E.N., and Zorin, V.V., Russ. J. Gen. Chem., 2017, vol. 87, no. 13, p. 3259. https://doi.org/10.1134/S1070363217130229

    Article  CAS  Google Scholar 

  14. Matsuda, T., Harada, T., Nakajima, Y., Itoh, T., and Nakamura, K., J. Org. Chem., 2000, vol. 65, p. 157.

    Article  CAS  PubMed  Google Scholar 

  15. Gašo-Sokač, D., Nujić, M., Bušić, V., and HabudaStanić, M., Croat. J. Food Sci. Technol., 2014, vol. 6, no. 1, p. 51.

    Google Scholar 

  16. Chanysheva, A.R., Vorob’eva, T.E., Sheiko, E.A., and Zorin, V.V., Bashk. Khim. Zh., 2018, vol. 25, no. 2, p. 41.

    CAS  Google Scholar 

  17. Chanysheva, A.R., Yunusova, G.V., Vorob’eva, T.E., and Zorin, V.V., Russ. J. Gen. Chem., 2016, vol. 86, no. 13, p. 3021. https://doi.org/10.1134/S107036321613017X

    Article  CAS  Google Scholar 

  18. Chanysheva, A.R., Sheiko, E.A., and Zorin, V.V., Russ. J. Gen. Chem., 2018, vol. 88, no. 13, p. 2934. https://doi.org/10.1134/S1070363218130170

    Article  CAS  Google Scholar 

  19. Chanysheva, A.R. and Zorin, V.V., Indian J. Chem., Sect. B, 2020, vol. 59, p. 1381.

    Google Scholar 

  20. Blake, J.F., Xu, R., Bencsik, J.R., and Xiao, D., J. Med. Chem., 2012, vol. 55, p. 8110.

    Article  CAS  PubMed  Google Scholar 

  21. Fournier, A.M., Brown, R.A., Farnaby, W., Miyatake-Ondozabal, H., and Clayden, J., Org. Lett., 2010, vol. 12, p. 2222. https://doi.org/10.1021/ol100627c

    Article  CAS  PubMed  Google Scholar 

  22. Chanysheva, A.R., Vorobyova, T.E., and Zorin, V.V., Tetrahedron, 2019, vol. 75, article ID 130494.

  23. Zorin, V.V., Petukhova, N.I., Shakhmaev, R.N, Vasilova, L.Ya., and Chanysheva, A.R., Osnovy issledovanii v oblasti stereo- i regionapravlennogo biokataliza i organicheskogo sinteza biologicheski aktivnykh veshchestv (Fundamentals of Studies in the Field of Stereo- and Regioselective Biocatalysis and Organic Synthesis of Biologically Active Compounds), Ufa: Ufimsk. Gos. Neft. Tekh. Univ.

Download references

Funding

This study was performed in the framework of state assignment of the Ministry of Science and Higher Education of the Russian Federation.

Author information

Authors and Affiliations

  1. Ufa State Petroleum Technological University, 450062, Ufa, Russia

    A. R. Chanysheva, E. A. Sheiko & V. V. Zorin

Authors
  1. A. R. Chanysheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. A. Sheiko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. V. Zorin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. R. Chanysheva.

Ethics declarations

No conflict of interest was declared by the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chanysheva, A.R., Sheiko, E.A. & Zorin, V.V. Asymmetric Bioreduction of 4-Chloroacetophenone Catalyzed by Daucus carota Cells in Water and Organic Solvents. Russ J Gen Chem 91, 2953–2956 (2021). https://doi.org/10.1134/S1070363221130247

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363221130247

Keywords:

Search

Navigation