7α-Hydroxylation of steroid 5-olefins by mold fungi
2010
Andryushina, V. A. | Druzhinina, A. V. | Yaderets, V. V. | Stytsenko, T. S. | Voishvillo, N. E.
Hydroxylation activity of the mold fungi belonging to the orders Dothideales, Hypocreales, and Mucorales towards Δ⁵-3β-hydroxysteroids was studied. The fungi Bipolaris sorokiniana, Fusarium sp., and Rhizopus nigricans were able to introduce hydroxy group at position 7α; however, this ability was detected only at a low substrate load and with a low yield. A 7α-hydroxylase activity of the Curvularia lunata VKPM F-981 culture was shown for the first time. It was demonstrated that the studied strain was capable of stereo- and regioselective transformations of androstane 5-olefins at a load not less than 2 g/1. Conversion of pregnane steroids by this culture yielded both 7α- and 11β-hydroxy derivatives. The introduction of 7α-hydroxy group by this strain occurred concurrently with enzymatic hydrolysis of ester groups, which proceeded under mild conditions to give the corresponding alcohols in the cases of both 3-acetate of Δ⁵-androstenes and mono- and triacetates of Δ⁵-pregnenes.
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