Highly Regioselective and Stereoselective Biohydroxylations of Oxandrolone
Microbially catalyzed reactions are a powerful and valuable tool for organic synthesis of many compounds with potential biological activity. Herein, we report efficient hydroxylations of the steroidal anabolic-androgenic lactone, oxandrolone, in the cultures of three strains of fungi, <i>Fusar...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-12-01
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| Series: | Catalysts |
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| Online Access: | https://www.mdpi.com/2073-4344/11/1/16 |
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| author | Paulina Łyczko Anna Panek Alina Świzdor |
| author_facet | Paulina Łyczko Anna Panek Alina Świzdor |
| author_sort | Paulina Łyczko |
| collection | DOAJ |
| description | Microbially catalyzed reactions are a powerful and valuable tool for organic synthesis of many compounds with potential biological activity. Herein, we report efficient hydroxylations of the steroidal anabolic-androgenic lactone, oxandrolone, in the cultures of three strains of fungi, <i>Fusarium culmorum</i>, <i>Mortierella isabellina</i>, and <i>Laetiporus sulphureus</i>. These reactions resulted in the production of four metabolites identified as 12β-hydroxyoxandrolone (<b>2</b>), 9α-hydroxyoxandrolone (<b>3</b>), 6α-hydroxyoxandrolone (<b>4</b>), and 15α-hydroxyoxandrolone (<b>5</b>), the latter being a new compound. The high substrate conversion rates and the product yields achieved indicate that these strains offer a new way to generate steroidal hydroxylactones with potential pharmaceutical interest. The structures of the isolated derivatives were characterized on the basis of spectroscopic data. The effect of modification of the A-ring structure of the steroid by the lactone group on the selectivity of hydroxylation in cultures of the tested fungi is also discussed. |
| first_indexed | 2024-03-10T13:47:00Z |
| format | Article |
| id | doaj.art-f3e958b686864ba69348039ba65240dd |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T13:47:00Z |
| publishDate | 2020-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-f3e958b686864ba69348039ba65240dd2023-11-21T02:32:39ZengMDPI AGCatalysts2073-43442020-12-011111610.3390/catal11010016Highly Regioselective and Stereoselective Biohydroxylations of OxandrolonePaulina Łyczko0Anna Panek1Alina Świzdor2Department of Chemistry, Wrocław University of Environmental and Life Sciences, 50-375 Wrocław, PolandDepartment of Chemistry, Wrocław University of Environmental and Life Sciences, 50-375 Wrocław, PolandDepartment of Chemistry, Wrocław University of Environmental and Life Sciences, 50-375 Wrocław, PolandMicrobially catalyzed reactions are a powerful and valuable tool for organic synthesis of many compounds with potential biological activity. Herein, we report efficient hydroxylations of the steroidal anabolic-androgenic lactone, oxandrolone, in the cultures of three strains of fungi, <i>Fusarium culmorum</i>, <i>Mortierella isabellina</i>, and <i>Laetiporus sulphureus</i>. These reactions resulted in the production of four metabolites identified as 12β-hydroxyoxandrolone (<b>2</b>), 9α-hydroxyoxandrolone (<b>3</b>), 6α-hydroxyoxandrolone (<b>4</b>), and 15α-hydroxyoxandrolone (<b>5</b>), the latter being a new compound. The high substrate conversion rates and the product yields achieved indicate that these strains offer a new way to generate steroidal hydroxylactones with potential pharmaceutical interest. The structures of the isolated derivatives were characterized on the basis of spectroscopic data. The effect of modification of the A-ring structure of the steroid by the lactone group on the selectivity of hydroxylation in cultures of the tested fungi is also discussed.https://www.mdpi.com/2073-4344/11/1/16biotransformationoxandrolonesteroidal hydroxylactonesstereoselective hydroxylations<i>Fusarium culmorum</i><i>Mortierella isabellina</i> |
| spellingShingle | Paulina Łyczko Anna Panek Alina Świzdor Highly Regioselective and Stereoselective Biohydroxylations of Oxandrolone Catalysts biotransformation oxandrolone steroidal hydroxylactones stereoselective hydroxylations <i>Fusarium culmorum</i> <i>Mortierella isabellina</i> |
| title | Highly Regioselective and Stereoselective Biohydroxylations of Oxandrolone |
| title_full | Highly Regioselective and Stereoselective Biohydroxylations of Oxandrolone |
| title_fullStr | Highly Regioselective and Stereoselective Biohydroxylations of Oxandrolone |
| title_full_unstemmed | Highly Regioselective and Stereoselective Biohydroxylations of Oxandrolone |
| title_short | Highly Regioselective and Stereoselective Biohydroxylations of Oxandrolone |
| title_sort | highly regioselective and stereoselective biohydroxylations of oxandrolone |
| topic | biotransformation oxandrolone steroidal hydroxylactones stereoselective hydroxylations <i>Fusarium culmorum</i> <i>Mortierella isabellina</i> |
| url | https://www.mdpi.com/2073-4344/11/1/16 |
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