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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
L. M. Kogan, E. A. Elin, V. I. Mel'nikova, and I. V. Torgov, KhPS [Chemistry of Natural Compounds], 5, 149, 1969.
A. A. Akhrem and Yu. A. Titov, Microbiological Transformations of Steroids [in Russian], Moscow, 1965.
L. M. Kogan and E. A. Yelin, The IInd International Congress on Hormonal Steroids, Milan, no. 412, 1966.
Wada Shun-yo, J. Pharmac. Soc. Japan, 79, 684, 1959.
R. Deghenghi, C. Revesz, and R. Gaudry, J. Med. Chem., 6, 301, 1961.
B. Kadis, Biochemistry, 5, 3604, 1966.
S. Rakhit and Ch. R. Engel, Can. J. Chem., 40, 2163, 1962.
J. K. Norymberski and G. F. Woods, J. Chem. Soc., 3426, 1955.
O. Mancera, G. Rosenkranz, and F. Sondheimer, J. Chem. Soc., 2189, 1953.
L. Fieser and M. Fieser, The Chemistry of Natural Products related to Phenanthrene [Russian translation], Moscow-Leningrad, 418, 1953.
N. S. Wulfson, V. I. Zaretskii, V. G. Zaikin, G. M. Segal, I. V. Torgov, and T. P. Fradkina, Tetrah. Let., 3015, 1964.
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.
A. Wettestein, Helv. Chim. Acta, 27, 1803, 1944.
A. D. Cross and C. Beard, J. Am. Chem. Soc., 86, 5317, 1964.
K. M. Wellman and C. Djerassi, J. Am. Chem. Soc., 87, 60, 1965.
N. L. Allinger, P. Crabbe, and G. Perez, Tetrah., 22, 1615, 1966.
J. C. Danilewicz and W. Klyne, J. Chem. Soc., 1306, 1965.
G. Amiard, M. Legrand, J. Mathieu, R. Heymes, and Truong van Truong, Bull. Soc. Chim. France, 2417, 1961.
P. N. Rao, J. Org. Chem., 26, 2149, 1961.
J. C. Danilewicz, D. C. F. Garbutt, A. Horeau, and W. Klyne, J. Chem. Soc., 2254, 1964.
A. Horeau and H. B. Kagan, Tetrah., 20, 2431, 1964.
I. I. Zaretskaya, L. M. Kogan, O. B. Tikhomirova, and I. V. Torgov, KhPS [Chemistry of Natural Compounds], 2, 321, 1966.
Author information
Authors and Affiliations
Additional information
Khimiya Prirodnykh Soedinenii, Vol. 6, No. 1, pp. 38–47, 1970
Rights and permissions
About this article
Cite this article
Kogan, L.M., Elin, É.A., Krishnamurti, M. et al. A further study of the substrate specificity in the reduction of 20-oxosteroids with a culture ofActinomyces roseochromogenus . Chem Nat Compd 6, 35–41 (1970). https://doi.org/10.1007/BF00564154
Published:
Issue Date:
DOI: https://doi.org/10.1007/BF00564154