32326-39-9Relevant academic research and scientific papers
Microbial Baeyer-Villiger oxidation of steroidal ketones using Beauveria bassiana: Presence of an 11α-hydroxyl group essential to generation of D-homo lactones
?wizdor, Alina,Ko?ek, Teresa,Panek, Anna,Bia?on?ska, Agata
experimental part, p. 253 - 262 (2012/03/10)
This paper demonstrates for the first time transformation of a series of 17-oxo steroidal substrates (epiandrosterone, dehydroepiandrosterone, androstenedione) by the most frequently used whole cell biocatalyst, Beauveria bassiana, to 11α-hydroxy-17a-oxa-d-homo-androst-17-one products, in the following sequence of reactions: 11α-hydroxylation and subsequent Baeyer-Villiger oxidation to a ring-D lactone. 11α-Hydroxyprogesterone, the product of the first stage of the progesterone metabolism, was further converted along two routes: hydroxylation to 6β,11α- dihydroxyprogesterone or 17β-acetyl chain degradation leading to 11α-hydroxytestosterone, the main metabolite of the substrate. Part of 11α-hydroxytestosterone underwent a rare reduction to 11α-hydroxy- 5β-dihydrotestosterone. The experiments have demonstrated that the Baeyer-Villiger monooxygenase produced by the strain catalyzes solely oxidation of C-20 or C-17 ketones with 11α-hydroxyl group. 17-Oxo steroids, beside the 11α-hydroxylation and Baeyer-Villiger oxidation, also underwent reduction to 17β-alcohols; activity of 17β-hydroxysteroid dehydrogenase (17β-HSD) has significant impact on the amount of the formed ring-D δ-lactone.
The hydroxylation of Δ5-androstenes by Cephalosporium aphidicola
Bensasson, Caroline M.,Hanson, James R.,Hunter, A. Christy
, p. 2355 - 2358 (2007/10/03)
Whereas the major hydroxylation product of 3β-hydroxy-5α-androstan- 17-one by Cephalosporium aphidicola is the 11α-alcohol, the presence of a Δ5-double bond in the substrate leads to non-stereospecific allylic hydroxylation at C-7. Hydroxylation at C-11 became a minor transformation and there was no detectable hydroxylation at C-14.
The hydroxylation of some 13α-methylsteroids by Cephalosporium aphidicola
Boynton, Juliette,Hanson, James R.,Hunter, A. Christy
, p. 951 - 956 (2007/10/03)
The Fungus, Cephalosporium aphidicola, has been shown to hydroxylate 5α,13α-androstan-3,17-dione and the 3β-alcohol at the C-1α and C-7α positions, whereas the corresponding compounds in the normal 13β-methyl series are hydroxylated at the C-11α and C-14α positions. Both series were hydroxylated at the 5α position. There was some epimerization of the axial 3α-alcohols to the equatorial 3β-epimers.
