Hydroxyl groups at C-3 and at C-17 of the unnatural enantiomer, ent-androsta-5,9(11)-diene-3 beta,17 beta-diol are oxidised by cholesterol oxidase from Rhodococcus erythropolis

Authors
Kitamoto, D Dieth, S Burger, A Tritsch, D Biellmann, JF
Citation
D. Kitamoto et al., Hydroxyl groups at C-3 and at C-17 of the unnatural enantiomer, ent-androsta-5,9(11)-diene-3 beta,17 beta-diol are oxidised by cholesterol oxidase from Rhodococcus erythropolis, TETRAHEDR L, 42(3), 2001, pp. 505-507
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
3
Year of publication
2001
Pages
505 - 507
Database
ISI
SICI code
0040-4039(20010115)42:3<505:HGACAA>2.0.ZU;2-E
Abstract
The ent-androsta-4,9(11)-diene-3 beta ,17 beta -diol 1b and ent-androsta-5, 9(11)-diene-3 beta ,17 beta -diol 2b prepared from chiral dione 3, were oxi dised by cholesterol oxidase with kinetic parameters close to those of the natural steroids la and 2a. In the preparative oxidation the final product was ent-androsta-4,9(11)-diene-3,17-dione 5. So the enzyme catalysed the ox idation of the hydroxyl groups at C-3 and C-17, whereas the natural enantio mers were only oxidised at C-3. (C) 2001 Elsevier Science Ltd. All rights r eserved.