Chemistry of Natural Compounds

, Volume 6, Issue 1, pp 35–41 | Cite as

A further study of the substrate specificity in the reduction of 20-oxosteroids with a culture ofActinomyces roseochromogenus

  • L. M. Kogan
  • É. A. Elin
  • M. Krishnamurti
  • I. V. Torgov
Article
  • 30 Downloads

Conclusions

A culture ofActinomyces roseochromogenus ATCC 3347 reduces 17-hydroxy- and 16α, 17α-epoxy-20-oxopregnenes to the corresponding 20α-alcohols, but is incapable of reducing 17α-acetoxy-, 17α-methyl-, and 16β-methylprogesterones or 17-unsubstituted 20-oxopregnenes. The results obtained show that the presence of the side chain in a conformation favorable for the formation of 20α-alcohols in the reduction of 20-oxosteroids with complex metal hydrides is in itself insufficient for the reduction of the 20-oxosteroids by a culture ofActinomyces roseochromogenus, which also reduces the 20-oxo group of 17α-pregnenes.

Keywords

Intramolecular Hydrogen Bond Sodium Borohydride Manganese Dioxide Activity Grade Isonicotinic Acid 

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References

  1. 1.
    L. M. Kogan, E. A. Elin, V. I. Mel'nikova, and I. V. Torgov, KhPS [Chemistry of Natural Compounds], 5, 149, 1969.Google Scholar
  2. 2.
    A. A. Akhrem and Yu. A. Titov, Microbiological Transformations of Steroids [in Russian], Moscow, 1965.Google Scholar
  3. 3.
    L. M. Kogan and E. A. Yelin, The IInd International Congress on Hormonal Steroids, Milan, no. 412, 1966.Google Scholar
  4. 4.
    Wada Shun-yo, J. Pharmac. Soc. Japan, 79, 684, 1959.CrossRefGoogle Scholar
  5. 5.
    R. Deghenghi, C. Revesz, and R. Gaudry, J. Med. Chem., 6, 301, 1961.CrossRefGoogle Scholar
  6. 6.
    B. Kadis, Biochemistry, 5, 3604, 1966.CrossRefGoogle Scholar
  7. 7.
    S. Rakhit and Ch. R. Engel, Can. J. Chem., 40, 2163, 1962.CrossRefGoogle Scholar
  8. 8.
    J. K. Norymberski and G. F. Woods, J. Chem. Soc., 3426, 1955.Google Scholar
  9. 9.
    O. Mancera, G. Rosenkranz, and F. Sondheimer, J. Chem. Soc., 2189, 1953.Google Scholar
  10. 10.
    L. Fieser and M. Fieser, The Chemistry of Natural Products related to Phenanthrene [Russian translation], Moscow-Leningrad, 418, 1953.Google Scholar
  11. 11.
    N. S. Wulfson, V. I. Zaretskii, V. G. Zaikin, G. M. Segal, I. V. Torgov, and T. P. Fradkina, Tetrah. Let., 3015, 1964.Google Scholar
  12. 12.
    W. Klyne, Optical rotation. In: Determination of Organic Structures by Physical Methods, ed. E. A. Braude and F. C. Nachod, Academic Press, New York, 1955.Google Scholar
  13. 13.
    A. Wettestein, Helv. Chim. Acta, 27, 1803, 1944.CrossRefGoogle Scholar
  14. 14.
    A. D. Cross and C. Beard, J. Am. Chem. Soc., 86, 5317, 1964.CrossRefGoogle Scholar
  15. 15.
    K. M. Wellman and C. Djerassi, J. Am. Chem. Soc., 87, 60, 1965.CrossRefGoogle Scholar
  16. 16.
    N. L. Allinger, P. Crabbe, and G. Perez, Tetrah., 22, 1615, 1966.CrossRefGoogle Scholar
  17. 17.
    J. C. Danilewicz and W. Klyne, J. Chem. Soc., 1306, 1965.Google Scholar
  18. 18.
    G. Amiard, M. Legrand, J. Mathieu, R. Heymes, and Truong van Truong, Bull. Soc. Chim. France, 2417, 1961.Google Scholar
  19. 19.
    P. N. Rao, J. Org. Chem., 26, 2149, 1961.CrossRefGoogle Scholar
  20. 20.
    J. C. Danilewicz, D. C. F. Garbutt, A. Horeau, and W. Klyne, J. Chem. Soc., 2254, 1964.Google Scholar
  21. 21.
    A. Horeau and H. B. Kagan, Tetrah., 20, 2431, 1964.CrossRefGoogle Scholar
  22. 22.
    I. I. Zaretskaya, L. M. Kogan, O. B. Tikhomirova, and I. V. Torgov, KhPS [Chemistry of Natural Compounds], 2, 321, 1966.Google Scholar

Copyright information

© Consultants Bureau 1972

Authors and Affiliations

  • L. M. Kogan
    • 1
  • É. A. Elin
    • 1
  • M. Krishnamurti
    • 1
  • I. V. Torgov
    • 1
  1. 1.Institute of the Chemistry of Natural Compounds, AS USSRUSSR

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