Microbial hydroxylation of 13-ethyl-17β-hydroxy-18,19-dinor-17α- pregn-4-en-20-yn-3-one

Steroids

Volumn 61, Issue 7, 1996, Pages 407-410

  Hu, Shang Hui ^a   Tian, Xu Fang ^a   Sun, Yu Hua ^a   Han, Guang Dian ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

13 ethyl 17 hydroxy 18,19 dinor 17 pregn 4 en 20 yn 3 one, 7 and 10 hydroxy derivatives; Aspergillus ochraceus; microbial hydroxylation; Rhizopus arrhizus

Indexed keywords

GESTAGEN; PROGESTERONE DERIVATIVE;

ARTICLE; ASPERGILLUS OCHRACEUS; BACTERIAL METABOLISM; BIOTRANSFORMATION; CHEMICAL REACTION; HYDROXYLATION; RHIZOPUS;

EID: 0030199631     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0039-128X(96)00047-5     Document Type: Article

References (11)

1. 1. De Jager E (1982). A new progestagen for oral contraception. Contracept Delivery Syst 3:11-15.
2. 2. Van den Heuvel MJ, Van Bokhoven CW, de Jong HP, Zeelen FJ (1988). A partial synthesis of 13-ethyl-11-méthylene-18,19-dinor-17α-pregn-4-en-20-yn-17-ol (desogestrel) based upon intramolecular oxidation of an 11β-hydroxy-19-norsteroid to the 18 → 11β-lactone. Recl Trav Chim Pays-Bas 107:331-334.
3. 3. Schwarz S, Ring S, Weber G, Teichmüller Palmer H-J, Pfeiffer C, Undentsch B, Erhart B, Grawe D (1994). Synthesis of 13-Ethyl-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-17-ol (desogestrel) and its main metabolite 3-oxo desogestrel. Tetrahedron 50:10709-10720.
4. 4. De Flines J, Van der Waard, Mils WJ, Szpilfogel SA (1963). Microbiological conversion of 19-nortestosterone (II) 10-and 11-hydroxylation. Recueil 82:129-137.
5. 13C NMR spectra of 17α-ethinyl-19-nortestosterone derivatives. Magn Reson Chem 28:656-658.
6. 13C N.M.R. spectra of steroids - a survey and commentary. Org Magn Reson 9:439-464.
7. 7. Hu S-h, Genain G, Azerad R (1995). Microbial transformation of steroids: contribution to 14α-hydroxylations. Steroids 60:337-352.
8. 8. Krischenowski D, Kieslich K (1993). Two novel microbial conversion products of progesterone derivatives. Steroids 58:278-281.
9. 9. Smith KE, Latif S, Kirk DN (1989). Microbial transformations of steroids. V. Transformation of progesterone by whole cells and extracts of Botryosphaerica obtusa. J Steroid Biochem 32:445-451.
10. 1H NMR spectra of the steroids hormones, their hydroxylated derivatives, and the related compounds. J Chem Soc (Perkin 2) 1567-1594.
11. 11. Perderson RL, Campbell JA, Babcock JC, Eppstein SH, Murray HC, Weintraub A, Meeks RC, Meister PD, Reineke LM, Peterson DH (1956). Microbial transformation of steroids. XIV. The preparation of a tertiary hydroxy steroid, 10ξ-hydroxy-19-nortestosterone. J Am Chem Soc 78:1512-1513.