Isaria fumosorosea KCh J2 Entomopathogenic Strain as an Effective Biocatalyst for Steroid Compound Transformations.
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ABSTRACT: The catalytic activity of enzymes produced by an entomopathogenic filamentous fungus (Isaria fumosorosea KCh J2) towards selected steroid compounds (androstenedione, adrenosterone, progesterone, 17?-methyltestosterone and dehydroepiandrosterone) was investigated. All tested substrates were efficiently transformed. The structure of the substrate has a crucial impact on regio- and stereoselectivity of hydroxylation since it affects binding to the active site of the enzyme. Androstenedione was hydroxylated in the 7?-position to give a key intermediate in the synthesis of the diuretic-7?-hydroxyandrost-4-ene-3,17-dione with 82% conversion. Adrenosterone and 17?-methyltestosterone were hydroxylated in the 6?-position. Hydroxylated derivatives such as 15?-hydroxy-17?-methyltestosterone and 6?,12?-dihydroxy-17?-methyltestosterone were also observed. In the culture of Isaria fumosorosea KCh J2, DHEA was effectively hydroxylated in the C-7 position and then oxidized to give 7-oxo-DHEA, 3?,7?- and 3?,7?-dihydroxy-17a-oxa-d-homo-androst-5-ene-17-one. We obtained 7?-OH-DHEA lactone with 82% yield during 3 days transformation of highly concentrated (5 g/L) DHEA.
SUBMITTER: Kozlowska E
PROVIDER: S-EPMC6151793 | biostudies-literature |
REPOSITORIES: biostudies-literature
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