Skip to main content
SpringerLink
Log in

Mikrobiologische Reaktionen

Seitenketten-Abbau und Dehydrierung bei Steroiden

  • Kurze Mitteilungen
  • Published:
Experientia Aims and scope Submit manuscript

Summary

Certain fungi, especially of the genusFusarium, are capable of rapidly degrading the side chain of 20-keto-pregnenes to the corresponding 17-ketones and, simultaneously, of dehydrogenating ringA. ThusΔ 1,4-3,17-diketo-androstadiene is formed almost quantitatively fromΔ 4-3,20-diketo-pregnenes and fromΔ 4-3,17-diketo-androstene, and in lower yields from the analogousΔ 5-3β-hydroxy compounds. The side chain of saturated 3-keto- or 3β-hydroxy-allopregnane-20-ones is also degraded quickly, but dehydrogenation in ringA proceeds more slowly. 17α-hydroxy-groups prevent the degradation of the side chain.

By means of this microbiological process in combination withInhoffen's aromatisation reaction, progesterone can be transformed in only two steps into estrone.

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

References

  1. Literatur zum Beispiel beiD. H. Peterson, Research6, 309 (1953).

    CAS  Google Scholar 

  2. R. Neher undA. Wettstein, Helv. chim. Acta35, 276 (1952).

    Article  CAS  Google Scholar 

  3. H. H. Inhoffen, Ang. Chemie53, 471 (1940);59, 207 (1947).

    Article  CAS  Google Scholar 

  4. E. B. Hersberg, M. Rubin undE. Schwenk, J. Org. Chem.15, 292 (1950).

    Article  Google Scholar 

  5. R. Neher undA. Wettstein, Helv. chim. Acta35, 276 (1952).

    Article  CAS  Google Scholar 

  6. System Propylenglykol-Toluol s.R. B. Burton, A. Zaffaroni undE. H. Keutmann, J. Biol. Chem.188, 763 (1951); System A und B3 s.J. E. Bush, Biochem. J.50, 370 (1952).

    Article  CAS  PubMed  Google Scholar 

  7. R. Neher undA. Wettstein, Helv. chim. Acta34, 2278 (1951).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Pharmazeutische Abteilung, Forschungslaboratorien der Ciba Aktiengesellschaft, Basel

    E. Vischer & A. Wettstein

Authors
  1. E. Vischer
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. Wettstein
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

2. Mitt.; auszugsweise vorgetragen am 6. September 1953 vor der Schweizerischen Chemischen Gesellschaft, Lugano; 1. Mitt. s. Exper.8, 422 (1952).

Gleichzeitig 119. Mitt.Über Steroide; 118. Mitt. s. Helv. chim. Acta36, Fasc.6, im Druck (1953).

Rights and permissions

Reprints and permissions

About this article

Cite this article

Vischer, E., Wettstein, A. Mikrobiologische Reaktionen. Experientia 9, 371–372 (1953). https://doi.org/10.1007/BF02167636

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02167636

Search

Navigation