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Transformation of dehydroepiandrosterone and pregnenolone by Mucor piriformis

Madyastha, KM and Joseph, T (1995) Transformation of dehydroepiandrosterone and pregnenolone by Mucor piriformis. In: Applied Microbiology and Biotechnology, 44 (3-4). 339-343 .

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The mode of transformation of dehydroepiandrosterone (I, 3 beta-hydroxyandrost-5-en-17-one) and pregnenolone (II, 3 beta-hydroxypregn-5-en-20-one) was studied using Mucor piriformis. Biotransformation products formed from I were 3 beta,17 beta-dihydroxyandrost-5-ene (Ia), 3 beta-hydroxyandrost-5-ene-7,17-dione (Ib), 3 beta,17 beta-dihydroxyandrost-5-en-7-one (Ic), 3 beta,7 alpha-dihydroxyandrost-5-en-17-one (Id) and 3 beta,7 alpha,17 beta-trihydroxyandrost-5-ene (Ie). Biotransformation products formed from compound II were 3 beta,7 alpha-dihydroxypregn-5-en-20-one (IIa) and 3 beta,7 alpha,11 alpha-trihydroxypregn-5-en-20-one (IIb). The organism did not carry out isomerization of the 5-en-3 beta-ol to a 4-en-3-one system in the steroid molecules tested. In addition, it failed to carry out 14 alpha-hydroxylation possibly because of the lack of a 4-en-3-one system in I and II, and stereospecific hydroxylation at the C-7 position in I and II.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Springer.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Ms V Mangala
Date Deposited: 27 May 2011 06:44
Last Modified: 27 May 2011 06:44
URI: http://eprints.iisc.ac.in/id/eprint/37983

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