Skip to main content
SpringerLink
Log in

Microbiological transformation of nitrogen-containing heterocyclic compounds. 3. Microbiological synthesis of hydroxy derivatives of 1-benzoylpiperidine and 1-benzoylpyrrolidine

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The microbiological transformation of 1-benzoylpiperidine and 1-benzoylpyrrolidine by cultures of the fungi Aspergillus niger VKM F-1119 and Cunninghamella verticillala VKPM F-430 proceeds regio- and stereospecificall and leads respectively to the 4- and 3-hydroxy derivatives in 40–80% yield. The spectrometric properties of these compounds were studied.

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

Similar content being viewed by others

Literature cited

  1. Yu. A. Ovchinnikov, Bioorganic Chemistry [in Russian], Prosveshchenie, Moscow (1987), pp. 644, 662.

    Google Scholar 

  2. M. S. Malik, N. K. Sangwan, and S. N. Rastogi, Chim. Acta Turc., 14, No. 3, 307 (1986).

    Google Scholar 

  3. D. M. Flanagan and M. M. Joullie, Heterocycles, 26, No. 8, 2247 (1987).

    Google Scholar 

  4. A. D. Cale, US Patent 4,705,853 (1987); Chem. Abstr., 109, 231,085 (1988).

    Google Scholar 

  5. G. W. J. Fleet, A. Karpas, R. A. Dwek, L. E. Fellows, A. S. Tyms, S. Petursson, S. K. Namgoong, N. G. Ramsden and P. W. Smith, FEBS Lett., 237, No. 1/2, 128 (1988).

    Google Scholar 

  6. B. D. Walker, M. Kowalski, W. C. Goh, K. Kozarsky, M. Krieger, C. Rosen, L. Rohrschneider, W. A. Haseltine, and J. Sodroski, Proc. Natl. Acad. Sci. USA, 84, No. 22, 8120 (1987).

    Google Scholar 

  7. N. Hamana, N. Ikota, and N. Ganem, J. Org. Chem., 52, 5492 (1987).

    Google Scholar 

  8. R. A. Johnson, M. E. Herr, H. C. Murray, and G. S. Fonken, J. Org. Chem., 34, No. 8, 3198 (1968).

    Google Scholar 

  9. A. Archelas, R. Furstoss, D. Srairi, and G. Maury, Bull. Soc. Chim. Fr., No. 2, 234 (1986).

    Google Scholar 

  10. D. Srairi and G. Maury, Bull. Soc. Chim. Fr., No. 2, 297 (1987).

    Google Scholar 

  11. L. V. Modyanova, L. I. Vorob'eva, O. I. Shibilkina, E. V. Dovgilevich, P. B. Terent'ev, and A. N. Kost, Biotechnologiya, No. 3, 24 (1990).

    Google Scholar 

  12. A. N. Kost, L. I. Vorob'eva, P. B. Terent'ev, L. V. Modyanova, O. I. Shibilkina, and L. A. Korosteleva, Prikladn. Biokhim. Mikrobiol., 13, No. 5, 696 (1977).

    Google Scholar 

  13. S. M. McElvain and R. E. McMahon, J. Am. Chem. Soc., 71, 901 (1949).

    Google Scholar 

  14. B. P. Mundi, B. R. Larsen, L. F. McKenzie, and G. Braden, J. Org. Chem., 37, No. 10, 1635 (1972).

    Google Scholar 

  15. P.B. Terent'ev and A. P. Stankyavinus, Mass Spectrometry of Biologically Active Nitrogenous Bases [in Russian], Mokslas, Vilnius (1987), p. 76.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Chemical and Biological Faculties, M. V. Lomonosov Moscow State University, USSR

    I. A. Parshikov, L. V. Modyanova, E. V. Dovgilivich, P. B. Terent'ev, L. I. Vorob'eva & G. V. Grishina

Authors
  1. I. A. Parshikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. V. Modyanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. V. Dovgilivich
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. P. B. Terent'ev
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. L. I. Vorob'eva
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. G. V. Grishina
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

For Communication 2, see Biotekhnologiya, No. 4, 24, 1990.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 195–199, February, 1992.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Parshikov, I.A., Modyanova, L.V., Dovgilivich, E.V. et al. Microbiological transformation of nitrogen-containing heterocyclic compounds. 3. Microbiological synthesis of hydroxy derivatives of 1-benzoylpiperidine and 1-benzoylpyrrolidine. Chem Heterocycl Compd 28, 159–162 (1992). https://doi.org/10.1007/BF00473936

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00473936

Keywords

Search

Navigation