Transformation of dehydroepiandrosterone and pregnenolone by Mucor piriformis |
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Authors: | K M Madyastha T Joseph |
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Institution: | (1) Department of Organic Chemistry, Bio-organic Section, Indian Institute of Science, 560 012 Bangalore, India |
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Abstract: | The mode of transformation of dehydroepiandrosterone (I, 3 -hydroxyandrost-5-en-17-one) and pregnenolone (II, 3 -hydroxypregn-5-en-20-one) was studied using Mucor piriformis. Biotransformation products formed from I were 3 ,17 -dihydroxyandrost-5-ene (Ia), 3 -hydroxyandrost-5-ene-7,17-dione (Ib), 3 ,17 -dihydroxyandrost-5-en-7-one (Ic), 3 ,7 -dihydroxyandrost-5-en-17-one (Ie). Biotransformation products formed from compound II were 3 ,7 -dihydroxypregn-5-en-20-one (IIa) and 3 ,7 ,11 -trihydroxypregn-5-en-20-one (IIb). The organism did not carry out isomerization of the 5-en-3 -ol to a 4-en-3-one system in the steroid molecules tested. In addition, it failed to carry out 14 -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. |
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