- Baeyer-villiger oxidation of some steroids by Aspergillus tamarii MRC 72400
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Biotransformations of epiandrosterone (1), dehydroepiandrosterone (2), testosterone (3), progesterone (4) and pregnenolone (5) by Aspergillus tamarii MRC 72400 for 5 days have been reported and the results of these incubations have been compared with previously published data obtained with Aspergillus tamarii QM 1223. A. tamarii MRC 72400 showed higher Bayer-Villiger monooxygenase activities than A. tamarii QM 1223 did. Apart from pregnenolone (5), A. tamarii MRC 72400 metabolized these steroids in different ways. Incubation of epiandrosterone (1) afforded 3β,11β-dihydroxy-5α-androstan-17- one (6) (3%) and 3β-hydroxy-17a-oxa-D-homo-5α-androstan-17-one (7) (9.5%). Incubation of dehydroepiandrosterone (2) afforded 3β-hydroxy-17a- oxa-D-homoandrost-5-en-17-one (8) (28%), testolactone (9) (6%), 3β,7β-dihydroxyandrost-5-en-17-one (10) (13%) and 3β,7α- dihydroxyandrost- 5-en-17-one (11) (24%). Incubation of testosterone (3) afforded testolactone (9) (58%). Incubation of progesterone (4) also afforded testolactone (9), however in higher yield (86%). Incubation of pregnenolone (5) afforded 3β-hydroxy-17a-oxa-D-homoandrost- 5-en-17-one (8) (25%) and testolactone (9) (27%).
- Yildirim, Kudret,Uzuner, Ahmet,Gulcuoglu, Emine Yasemin
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experimental part
p. 743 - 754
(2011/12/03)
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- SYNTHESIS OF 11-HYDROXYLATED ANDROSTANE DERIVATIVES
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Reaction conditions for selective reductions of 3- and 17-oxo groups are described and applied to syntheses of 11-hydroxylated derivatives.
- Fajkos, Jan,Joska, Jiri
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p. 1845 - 1849
(2007/10/02)
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