Stereoselective Luche Reduction of Deoxynivalenol and Three of Its Acetylated Derivatives at C8
The trichothecene mycotoxin deoxynivalenol (DON) is a well known and common contaminant in food and feed. Acetylated derivatives and other biosynthetic precursors can occur together with the main toxin. A key biosynthetic step towards DON involves an oxidation of the 8-OH group of 7,8-dihydroxycalon...
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MDPI AG
2014-01-01
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| Series: | Toxins |
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| Online Access: | http://www.mdpi.com/2072-6651/6/1/325 |
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| author | Philipp Fruhmann Christian Hametner Hannes Mikula Gerhard Adam Rudolf Krska Johannes Fröhlich |
| author_facet | Philipp Fruhmann Christian Hametner Hannes Mikula Gerhard Adam Rudolf Krska Johannes Fröhlich |
| author_sort | Philipp Fruhmann |
| collection | DOAJ |
| description | The trichothecene mycotoxin deoxynivalenol (DON) is a well known and common contaminant in food and feed. Acetylated derivatives and other biosynthetic precursors can occur together with the main toxin. A key biosynthetic step towards DON involves an oxidation of the 8-OH group of 7,8-dihydroxycalonectrin. Since analytical standards for the intermediates are not available and these intermediates are therefore rarely studied, we aimed for a synthetic method to invert this reaction, making a series of calonectrin-derived precursors accessible. We did this by developing an efficient protocol for stereoselective Luche reduction at C8. This method was used to access 3,7,8,15-tetrahydroxyscirpene, 3-deacetyl-7,8-dihydroxycalonectrin, 15-deacetyl-7,8-dihydroxycalonectrin and 7,8-dihydroxycalonectrin, which were characterized using several NMR techniques. Beside the development of a method which could basically be used for all type B trichothecenes, we opened a synthetic route towards different acetylated calonectrins. |
| first_indexed | 2024-04-11T21:37:31Z |
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| institution | Directory Open Access Journal |
| issn | 2072-6651 |
| language | English |
| last_indexed | 2024-04-11T21:37:31Z |
| publishDate | 2014-01-01 |
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| record_format | Article |
| series | Toxins |
| spelling | doaj.art-79543f022deb4001b3021a786496effb2022-12-22T04:01:41ZengMDPI AGToxins2072-66512014-01-016132533610.3390/toxins6010325toxins6010325Stereoselective Luche Reduction of Deoxynivalenol and Three of Its Acetylated Derivatives at C8Philipp Fruhmann0Christian Hametner1Hannes Mikula2Gerhard Adam3Rudolf Krska4Johannes Fröhlich5Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9, Vienna 1060, AustriaInstitute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9, Vienna 1060, AustriaInstitute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9, Vienna 1060, AustriaDepartment of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna (BOKU), Konrad Lorenz Str. 24, Tulln 3430, AustriaDepartment for Agrobiotechnology (IFA-Tulln), Center for Analytical Chemistry, University of Natural Resources and Life Sciences, Vienna (BOKU), Konrad Lorenz Str. 20, Tulln 3430, AustriaInstitute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9, Vienna 1060, AustriaThe trichothecene mycotoxin deoxynivalenol (DON) is a well known and common contaminant in food and feed. Acetylated derivatives and other biosynthetic precursors can occur together with the main toxin. A key biosynthetic step towards DON involves an oxidation of the 8-OH group of 7,8-dihydroxycalonectrin. Since analytical standards for the intermediates are not available and these intermediates are therefore rarely studied, we aimed for a synthetic method to invert this reaction, making a series of calonectrin-derived precursors accessible. We did this by developing an efficient protocol for stereoselective Luche reduction at C8. This method was used to access 3,7,8,15-tetrahydroxyscirpene, 3-deacetyl-7,8-dihydroxycalonectrin, 15-deacetyl-7,8-dihydroxycalonectrin and 7,8-dihydroxycalonectrin, which were characterized using several NMR techniques. Beside the development of a method which could basically be used for all type B trichothecenes, we opened a synthetic route towards different acetylated calonectrins.http://www.mdpi.com/2072-6651/6/1/325dihydroxycalonectrinstrichothecenesDONLuche reductionscirpene |
| spellingShingle | Philipp Fruhmann Christian Hametner Hannes Mikula Gerhard Adam Rudolf Krska Johannes Fröhlich Stereoselective Luche Reduction of Deoxynivalenol and Three of Its Acetylated Derivatives at C8 Toxins dihydroxycalonectrins trichothecenes DON Luche reduction scirpene |
| title | Stereoselective Luche Reduction of Deoxynivalenol and Three of Its Acetylated Derivatives at C8 |
| title_full | Stereoselective Luche Reduction of Deoxynivalenol and Three of Its Acetylated Derivatives at C8 |
| title_fullStr | Stereoselective Luche Reduction of Deoxynivalenol and Three of Its Acetylated Derivatives at C8 |
| title_full_unstemmed | Stereoselective Luche Reduction of Deoxynivalenol and Three of Its Acetylated Derivatives at C8 |
| title_short | Stereoselective Luche Reduction of Deoxynivalenol and Three of Its Acetylated Derivatives at C8 |
| title_sort | stereoselective luche reduction of deoxynivalenol and three of its acetylated derivatives at c8 |
| topic | dihydroxycalonectrins trichothecenes DON Luche reduction scirpene |
| url | http://www.mdpi.com/2072-6651/6/1/325 |
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