The conditions for preparing 14α-hydroxyandrostenedione - an intermediate in the synthesis of highly active gestagens - using the fungus Curvularia lunata CBE with an increased steroid substrate load of 5 g/liter in the presence of methylcyclodextrin were identified. The microbiological method of introducing 14α-hydroxy groups into the androstane structure has significant advantages over chemical approaches from the technical and ecological points of view and for obtaining a higher yield.
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References
P. M. Smid, W. J. Van Zoest, P. G. Weber, and A. F. Marx, US Patent 5093502 (1992).
M. Nakakoshi, Japanese patent 0576,387; Chem. Abstr., 119, 93698 (2004).
S. B. Mahato and S. Garai, Steroids, 62, 332–345 (1997).
P. Fernandes. A. Cruz, B. Angelova, et al., Enzyme Microbiol. Technol., 32(6), 688–705 (2003).
GB 1105980 Schering AG (1968).
A. F. St. Andre, H. B. MacPhillamy, J. A. Nelson, et al., J. Amer. Chem. Soc., 74(5), 5506–5511 (1952).
V. C. Njar, S. Shapiro, T. Arunachalam, and E. Caspi, J. Steroid Biochem., 22, 399 (1985).
K. Smith, D. Kirk, and S. Latif, J. Steroid Biochem., 32, 445–451 (1989).
A.Weber and M. Kennecke, Ger. Offen DE 4129005 A1; Chem. Abstr., 118, 190112p (1993).
K. M. Madiastha and T. Joseph, J. Steroid Biochem., 45, 563–569 (1993).
H. Yoshioka, H. Asuda, and S. Fojita. Eur. Patent 599568.
S. Hu, G. Genain, and R. Azerad, Steroids, 60, 337–352 (1995).
O. Schaff and K. Dettner, J. S Biochem. Mol. Biol., 67, 451–465 (1998).
N. E. Voishvillo, V. A. Andryushina, T. S. Savinova, and T. S. Stytsenko, Priklad. Biokhim. Microbiol., 40, 536–543 (2004).
G. A. Huppi and J. B. Siddall, US patent 3481926; Chem. Abstr., 72, 67214c (1970).
G. A. Huppi and J. B. Siddall, J. Amer. Chem. Soc., 89, 6790 (1967).
W. Van Bever, F. Kohen, V. V. Ranade, and R. E. Counsell, Chem. Commun., 758 (1970).
L. F. Fieser, J. Amer. Chem. Soc., 70, 3237 (1948).
S. D. Shuvalova, K. N. Gabinskaya, E. V. Popova, et al., Khim.-Farm. Zh., 35, No. 5, 44–46 (2001).
V. V. Yaderets, V. A. Andryushina, Yu. É. Bartoshevich, et al., Priklad. Biokhim. Microbiol., 43, No. 6, (2007).
H. Iizuka, A. Naito, and J. Sato, J. Gen. Appl. Microbiol., 7, 118 (1961).
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 43, No. 1, pp. 37–40, January, 2009.
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Yaderets, V.V., Andryushina, V.A., Voishvillo, N.E. et al. Studies of synthesis routes for biologically active 14α-hydroxylated steroids. Pharm Chem J 43, 55–58 (2009). https://doi.org/10.1007/s11094-009-0229-8
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DOI: https://doi.org/10.1007/s11094-009-0229-8