Flexibility of the endogenous progesterone lactonisation pathway in Aspergillus tamarii KITA: Transformation of a series of cortical steroid analogues

Journal of Steroid Biochemistry and Molecular Biology

Volumn 87, Issue 4-5, 2003, Pages 301-308

  Hunter, A Christy ^a   Carragher, Natasha E ^a  

^a UNIVERSITY OF BRIGHTON   (United Kingdom)

Author keywords

Aspergillus tamarii; Baeyer Villiger oxidation; Biotransformation; Cortical steroid; Epoxide opening; Lactonisation; Progesterone; Steroid

Indexed keywords

16BETA HYDROXY 17ALPHA OXA DEXTRO HOMOANDROST 4 EN 3,17 DIONE; 17ALPHA OXA DEXTRO HOMOANDROST 1,4 DIEN 3,17 DIONE; ANDROSTERONE DERIVATIVE; CORTICOSTEROID DERIVATIVE; CORTODOXONE; DEOXYCORTICOSTERONE; HYDROXYPROGESTERONE; LACTONE DERIVATIVE; PROGESTERONE; PROGESTERONE DERIVATIVE; TESTOLOLACTONE; UNCLASSIFIED DRUG;

ARTICLE; ASPERGILLUS; BAEYER VILLIGER REACTION; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; CORTICOSTEROID METABOLISM; FUNGAL STRAIN; LACTONIZATION; METABOLITE; NONHUMAN; PROGESTERONE METABOLISM; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; STEREOCHEMISTRY; STEROIDOGENESIS;

ASPERGILLUS; ASPERGILLUS TAMARII; FUNGI; HOMO;

EID: 0347362546     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2003.10.001     Document Type: Article

References (25)

1. Brannon D.R., Martin J., Oehlschlager A.C., Durham N.N., Zalkow L.H. Transformation of progesterone and related steroids by Aspergillus tamarii. J. Org. Chem. 30:1965;760-762.
2. Fonken G.S., Murray H.C., Reineke L.M. Pathway of progesterone oxidation by Cladosporium resinae. J. Am. Chem. Soc. 82:1960;5507-5508.
3. 19 ketones and to testololactone. J. Am. Chem. Soc. 75:1953;5768-5769.
4. Fried J., Thoma R.W., Klingsberg A. Oxydation of steroids by microorganisms. III Side chain degradation, ring D-cleavage and dehydrogenation in ring A. J. Am. Chem. Soc. 75:1953;5764-5765.
5. Mihovilovic M.D., Müller B., Stanley P. Monooxygenase-mediated Baeyer-Villiger oxidations. Eur. J. Org. Chem. 22:2002;3711-3730.
6. El-Tayeb O., Knight S.G., Sih C.J. Substrate specificity in steroid side-chain degradation by microorganisms. Biochim. Biophys. Acta. 93:1964;411-417.
7. El-Tayeb O., Knight S.G., Sih C.J. Steroid epoxide cleavage by Cylindrocarpon radicola. Biochim. Biophys. Acta. 93:1964;402-410.
8. Carlstrom K. Side chain degradation of epimeric 20-hydroxy-4-pregnene-3- ones by Penicillium lilacinium, NRRL 895. Acta Chem. Scand. 24:1970;1759-1767.
9. Brannon D.R., Parrish F.W., Wiley B.J., Long L. Microbial transformation of a series of androgens with Aspergillus tamarii. J. Org. Chem. 32:1967;1521-1527.
10. 1H NMR spectra of steroid hormones, their hydroxylated derivatives and related compounds J. Chem. Soc., Perkin Trans. 2:1990;1567-1594.
11. Hanson J.R., Hunter A.C. The microbiological hydroxylation of some steroids with cortical side chain by Cephalosporium aphidicola. Phytochemistry. 49(8):1998;2359-2362.
12. Rao P.N., Axelrod L.R. 17α,20α-Dihydroxy-4-pregnene-3-one. J. Org. Chem. 26:1961;2552-2553.
13. Bastard J., Fetizon M., Gramain J.C. Oxydations par le carbonate d'argent sur celite-VII Oxydations de dids. Tetrahedron. 29:1973;2867-2875.
14. Hanson J.R., Hunter A.C. The hydroxylation of steroidal ring D lactones by Cephalosporium aphidicola. Phytochemistry. 49(8):1998;2349-2353.
15. El-Tayeb O., Knight S.G., Sih C.J. Substrate specificity in steroid side-chain degradation by microorganisms. Biochim. Biophys. Acta. 93:1964;411-417.
16. Carvajal F., Vitale O.F., Gentles M.J., Herzog H.L., Hershberg E.B. Microbiological transformation of steroids VI Stereospecific reductions of the 20-carbonyl group. J. Org. Chem. 24:1960;695-698.
17. Nawa H., Uchibayashi M., Takeda R., Nakanishi I. Transformation of steroids by Pseudomonas. Tetrahedron. 4:1958;201-204.
18. Gorzynski Smith J. Synthetically useful reactions of epoxides. Synthesis. 8:1984;629-656.
19. 13-17α-pregneni ottenuti per riduzione con lievito fermentante. Gazz. Chim. Ital. 36:1956;1219-1225.
20. Procházkz Ž., Fajkoš J., Joska J., Šorm F. Microbial oxygenation of B-norsteroids Coll. Czech. Chem. Commun. 26:1961;2068-2070.
21. E.L. Eliel, S.H. Wilen, Stereochemistry of Organic Compounds, Wiley/Interscience, New York, 1994, pp. 587-588, ISBN 0-471-01670-5.
22. Weeks C.M., Duax W.L., Wolff M.E. A comparison of the molecular structures of six corticosteroids. J. Am. Chem. Soc. 95:1973;2865-2868.
23. Duax W.L., Griffin J.F., Rohrer D.C. Conformation of progesterone side chain: conflict between X-ray data and force-field calculations. J. Am. Chem. Soc. 103(22):1981;6705-6712.
24. Hazel J.P., Weeks C.M., Osawa Y. 16α,17α-Epoxypregnenolone monohydrate. Cryst. Struct. Commun. 5:1976;103-106.
25. Andrade L.C.R., Paixão J.A., de Almeida M.J.M., Martins R.M.L.M., Soares H.I.M., Morais G.J.R., Moreneo M.J.S.M., Sáe Melo M.L., Campos Neves A.S. 16α,17α-Epoxy-20-oxopregn-5-en-3β-yl acetate. Cryst. Struct. Comm. C57:2001;587-589.