Advertisement

Chemistry of Heterocyclic Compounds

, Volume 33, Issue 5, pp 523–526 | Cite as

Microbiological transformation of derivatives of 4-phenyl-2-pyrrolidone by mycelial fungi

  • I. A. Parshikov
  • P. B. Terent'ev
  • N. F. Piskunkova
  • R. A. Gracheva
  • G. A. Bulakhov
Article
  • 40 Downloads

Abstract

In the microbiological transformation of 4-phenylpyrrolidine by growing strains of the fungi Cunninghamella,Beauveria, andPenicillium, its 1-ethyl and 1-acetyl derivatives are formed; these are subsequently oxidized at positions 2 and 3. In contrast, 1-benzoyl-4-phenylpyrrolidine is hydroxylated by those same cultures in positions 3 and 5. For the corresponding 2-pyrrolidone derivatives, the 4-phenyl-2-pyrrolidone is not transformed by these fungi, while the 1-benzoyl-2-pyrrolidone is hydrolyzed at the benzamide group under the same conditions. The structures of the products from these transformations were determined by mass spectrometry.

Keywords

Mass Spectrometry Organic Chemistry Mycelial Fungus Benzamide Cunninghamella 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    E. V. Sharova, A. A. Potapov, and M. A. Kulikov, Zh. Nevropatol. Psikhot., No. 5, 42 (1988).Google Scholar
  2. 2.
    Yu. V. Gol'dblat and I. P. Lapin, Zh. Nevropatol. Psikhot. No. 8, 1146 (1986).Google Scholar
  3. 3.
    M. D. Mashkovskii, Pharmaceuticals [in Russian], Meditsina, Moscow (1993), Vol. 1, p. 138.Google Scholar
  4. 4.
    D. M. Flanagan and M. M. Joullie, Heterocycles,26, 2247 (1987).Google Scholar
  5. 5.
    I. A. Parshikov, P. B. Terent'ev, and L. V. Modyanova, Khim. Geterotsikl. Soedin., No. 11/12, 1510 (1994).Google Scholar
  6. 6.
    I. A. Parshikov, L. V. Modyanova, E. V. Dovgilevich, P. B. Terent'ev, L. I. Vorob'eva, and G. V. Grishina, Khim. Geterotsikl. Soedin., No. 2, 195 (1992).Google Scholar
  7. 7.
    I. A. Parshikov, L. I. Vorob'eva, L. V. Modyanova, E. V. Dovgilevich, and P. B. Terent'ev, USSR Inventor's Certificate 1,789,557; Byull. Izobret., No. 3 (1993).Google Scholar
  8. 8.
    P. B. Terent'ev, I. A. Parshikov, G. V. Grishina, N. F. Piskunkova, T. I. Chumakov, and G. A. Bulakhov, Khim. Geterotsikl. Soedin., No. 5, 711 (1997).Google Scholar
  9. 9.
    G. Schwarz and F. Lingens, in: Biochemical and Microbial Degradation, C. Ratlege (ed.), Dortrecht, Netherlands (1994), p. 459.Google Scholar
  10. 10.
    E. V. Dovgilevich, I. A. Parshikov, L. V. Modyanova, P. B. Terent'ev, and G. A. Bulakhov, Mendeleev Commun., No. 2, 42 (1991).Google Scholar
  11. 11.
    C. H. Wong and G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Pergamon Press, New York (1994).Google Scholar

Copyright information

© Plenum Publishing Corporation 1997

Authors and Affiliations

  • I. A. Parshikov
  • P. B. Terent'ev
  • N. F. Piskunkova
  • R. A. Gracheva
  • G. A. Bulakhov

There are no affiliations available

Personalised recommendations