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Steroid derivatives

LXXI. The microbial dehydrogenation of 17β-hydroxy-17α-methyl-5α-androstan-3-one

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Abstract

The microorganismsBacillus sphaericus, Septomyxa affinis andProactinomyces globerulus dehydrogenate 17β-hydroxy-17α-methyl-5α-androstan-3-one to corresponding 1-, or 1,4-unsaturated derivatives. However, the biotransformation of the cited compound byArthrobacter simplex andMycobacterium flavum simultaneously introduced one atom of oxygen into the 17a-position and resulted in the formation of 17β hydroxy-17α-methyl-17a-oxa-D-homo-5α-1-androsten-3-one.

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References

  • Čapek, A., Hanč, O., Kakáč, B.:Microbiological transformation of steroids. XVIII. Dehydrogenation of cortisone in position 1–2. Fol. microbiol. 7: 175, 1962.

    Article  Google Scholar 

  • Charney, W., Herzog, H. L.:Microbial transformations of steroids. Academic Press New York, 1967.

    Google Scholar 

  • Heller, M., Stolar, S. M., Bernstein, S.:16-Hydroxylated steroids. XX. Some transformations of 16β,21-diacetoxy-17α-hydroxypregn-4-ene-3,20-dione. J. org. Chem. 26: 5036, 1961.

    Article  CAS  Google Scholar 

  • Kluepfel, D., Coronelli, C.:The microbiological dehydrogenation of 16β-methyl-5α-dihydrocortisone. Experientia 18: 441, 1962.

    Article  PubMed  CAS  Google Scholar 

  • Mallett, G. E.: Δ1-Dehydrogenation of steroids by fermentation with Actinoplanes. US pat. 3,128,238, 1964.

  • Pettit, G. R., Kasturi, T. R., Green, B., Knight, J. C.:Steroids and related natural products. VI. Diborane reduction of lactones to cyclic hemiacetals. J. org. Chem. 26: 4773, 1961.

    Article  CAS  Google Scholar 

  • Ringold, H. J., Hayano, M., Stefanovic, V.:Concerning the stereochemistry and mechanism of the bacterial C-1,2-dehydrogenation of steroids. J. biol. Chem. 238: 1960, 1963.

    PubMed  CAS  Google Scholar 

  • Stefanovic, V., Hayano, M., Dorfman, R. I.:Some observation on the Δ 1-dehydrogenation of steroids by Bacillus sphaericus. Biochim. biophys. Acta 71: 429, 1963.

    Article  PubMed  CAS  Google Scholar 

  • Stoudt, T. H.:The microbial dehydrogenation of some pregnanes and allopregnanes to 1,4-pregnadienes. Arch. Biochem. Biophys. 74: 280, 1958.

    Article  PubMed  CAS  Google Scholar 

  • Stoudt, T. H.: Δ1-Dehydrosteroids US pat. 3,016,335, 1962.

  • Vischer, E., Wettstein, A.:Microbiological reactions, splitting of the side chain and dehydrogenation of steroids. Experientia 9: 371, 1953.

    Article  PubMed  CAS  Google Scholar 

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  1. Pharmaceutical and Biochemical Research Institute, 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 15, 318–324 (1970). https://doi.org/10.1007/BF02869061

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  • DOI: https://doi.org/10.1007/BF02869061

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