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Steroid derivatives

LXXVII. Microbial aromatization of steroid 19-hydroxy compounds and 1(10),5-dienes by the action of Proactinomyces globerulus

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Abstract

Microbial transformation of some steroid 19-hydroxy compounds and 1(10),5-dienes, substituted by a hydroxyl group in position 3, by the action ofProactinomyces globerulus, yielded substances with aromatic A ring. Substrates with 17-keto group underwent simultaneously a partial reduction resulting in the formation of 17β-hydroxyl.

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References

  • Amorosa M., Caglioti L., Cainelli G., Immer H., Keller J., Wehrli H., Mihailović M. L., Schaffner K., Arigoni D., Jeger O.: Über Steroide und Sexualhormone. 227. Mitt. Die Fragmentierung einwertiger Alkohole mit Blei(IV)-acetat.Helv. Chim. Acta 45, 2674 (1962).

    Article  CAS  Google Scholar 

  • Bagli J. F., Morand P. F., Wiesner K., Gaudry R.: A simple synthesis of equilin.Tetrahedron Letters 387, 1964.

  • Breed R. S. et al.:Bergey's Manual of Determinative Bacteriology. 7th edition. Baltimore, Williams & Wilkins Co., 1957.

    Google Scholar 

  • Brodie H. J., Possanza G., Townsley J. D.: Mechanism of estrogen biosynthesis. V. Stereochemical comparison of aromatization in placental and microbiological systems.Biochim. Biophys. Acta 152, 770 (1968).

    PubMed  CAS  Google Scholar 

  • Casas-Campillo C.: Cyclopentanopolyhydrophenanthrene derivatives.Franc. patent 1, 417, 023, 1965.

  • Coombe R. G., Tsang Y. Y., Hamilton P. B., Sih Ch. J.: Mechanism of steroid oxidation by microorganisms. X. Oxidative cleavage of estrone.J. Biol. Chem. 241, 1587 (1966).

    CAS  Google Scholar 

  • Denot E., Casas-Campillo C., Crabbe P.: Steroids CCCXXXIV. Preparation and microbiological transformation of some 19-substituted steroids.J. Europ. Steroids. 2, 495 (1967).

    CAS  Google Scholar 

  • Djerassi C., Engle R. R., Bowers A.: Direct conversion of steroidal Δ5-3β-alcohols to Δ5 and Δ4-3-steroids.J. Org. Chem. 21, 1547 (1956).

    Article  CAS  Google Scholar 

  • Dodson R. M., Muir R. D.: Microbiological transformations. II. The microbiological aromatization of steroids.J. Am. Chem. Soc. 80, 5004 (1958).

    Article  CAS  Google Scholar 

  • Dodson R. M., Muir R. D.: Microbiological transformations. VI. The microbiological aromatization of steroids.J. Am. Chem. Soc. 80, 5004 (1958).

    Article  CAS  Google Scholar 

  • Dodson R. M., Muir R. D.: Microbiological transformations. VI. The microbiological aromatization of steroids.J. Am. Chem. Soc. 83, 4627 (1961a).

    Article  CAS  Google Scholar 

  • Dodson R. M., Muir R. D.: Microbiological transformations. VII. The hydroxylation of steroids at C-9.J. Am. Chem. Soc. 83, 4631 (1961b).

    Article  CAS  Google Scholar 

  • Hauser D., Heusler K., Kalvoda J., Schaffner K., Jeger O.: Fragmentierungen und intramolekulare Abstraktionen tertiärer Wasserstoffatome ausgehend von primären Oxyradikalen mit fixierten Reaktionszentren.Helv. Chim. Acta 47, 1961 (1964).

    Article  CAS  Google Scholar 

  • Jacques J., Kagan H., Ourisson G., Allard S.: Selected constants. Optical rotatory power. Ia. Steroids.Pergamon Press 1965.

  • Míčková R., Syhora K.: Steroid derivatives. LXII. An anomalous debromination of 5,6-dibromides of estrane series.Coll. Czech. Chem. Commun. 34, 458 (1969).

    Google Scholar 

  • Sih Ch. J., Laval J.: Enzymic analysis of functional groups on the steroid nucleus.Biochim. Biophys. Acta 64, 409 (1962).

    Article  PubMed  CAS  Google Scholar 

  • Sih Ch. J., Lee S. S., Tsong Y. Y., Wang K. C.: 3,4-Dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione. An intermediate in the microbiological degradation of ring A of androst-4-ene-3,17-dione.J. Am. Chem. Soc. 87, 1385 (1965a).

    Article  CAS  Google Scholar 

  • Sih Ch. J., Lee S. S., Tsong Y. Y., Wang K. C., Chang F. N.: An efficient synthesis of estrone and 19-norsteroids from cholesterol.J. Am. Chem. Soc. 87, 2765 (1965b).

    Article  PubMed  CAS  Google Scholar 

  • Sih Ch. J., Wang K. C., Gibson D. T., Whitlock H. W.: On the mechanism of ring A cleavage in the degradation of 9,10-seco steroids by microorganisms.J. Am. Chem. Soc. 87, 1386 (1965c).

    Article  PubMed  CAS  Google Scholar 

  • Sih Ch. J., Wang K. C.: A new route to estrone from sterols.J. Am. Chem. Soc. 87, 1387 (1965)

    Article  PubMed  CAS  Google Scholar 

  • Syntex Corp.: Preparation of new Δ1(10),5-19-norsteroids. Neth. Appl. 6, 402, 644;Chem. Abstr. 62, 11874 (1965).

    Google Scholar 

  • Vezina C., Singh K.: Microbiological transformations of sterols. US patent 3,398,054, 1968.

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  1. Research Institute of Pharmacy and Biochemistry, 194 04, Prague 9

    J. Protiva & V. Schwarz

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  1. J. Protiva
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  2. V. Schwarz
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Protiva, J., Schwarz, V. Steroid derivatives. Folia Microbiol 19, 151–155 (1974). https://doi.org/10.1007/BF02872850

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  • DOI: https://doi.org/10.1007/BF02872850

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