Synthesis of zearalenone-16-β,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation
The development of a reliable procedure for the synthesis of the 16-glucoside and 16-sulfate of the resorcylic acid lactone (RAL) type compound zearalenone is presented. Different protective group strategies were considered and applied to enable the preparation of glucosides and sulfates that are di...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2014-05-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.112 |
| _version_ | 1818916452461182976 |
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| author | Hannes Mikula Julia Weber Dennis Svatunek Philipp Skrinjar Gerhard Adam Rudolf Krska Christian Hametner Johannes Fröhlich |
| author_facet | Hannes Mikula Julia Weber Dennis Svatunek Philipp Skrinjar Gerhard Adam Rudolf Krska Christian Hametner Johannes Fröhlich |
| author_sort | Hannes Mikula |
| collection | DOAJ |
| description | The development of a reliable procedure for the synthesis of the 16-glucoside and 16-sulfate of the resorcylic acid lactone (RAL) type compound zearalenone is presented. Different protective group strategies were considered and applied to enable the preparation of glucosides and sulfates that are difficult to access up to now. Acetyl and p-methoxybenzyl protection led to undesired results and were shown to be inappropriate. Finally, triisopropylsilyl-protected zearalenone was successfully used as intermediate for the first synthesis of the corresponding mycotoxin glucoside and sulfate that are highly valuable as reference materials for further studies in the emerging field of masked mycotoxins. Furthermore, high stability was observed for aryl sulfates prepared as tetrabutylammonium salts. Overall, these findings should be applicable for the synthesis of similar RAL type and natural product conjugates. |
| first_indexed | 2024-12-20T00:18:24Z |
| format | Article |
| id | doaj.art-e22719284d264779af3f611b623eccde |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-20T00:18:24Z |
| publishDate | 2014-05-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-e22719284d264779af3f611b623eccde2022-12-21T20:00:16ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-05-011011129113410.3762/bjoc.10.1121860-5397-10-112Synthesis of zearalenone-16-β,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugationHannes Mikula0Julia Weber1Dennis Svatunek2Philipp Skrinjar3Gerhard Adam4Rudolf Krska5Christian Hametner6Johannes Fröhlich7Institute of Applied Synthetic Chemistry, Vienna University of Technology (VUT), Getreidemarkt 9/163, A-1060 Vienna, AustriaInstitute of Applied Synthetic Chemistry, Vienna University of Technology (VUT), Getreidemarkt 9/163, A-1060 Vienna, AustriaInstitute of Applied Synthetic Chemistry, Vienna University of Technology (VUT), Getreidemarkt 9/163, A-1060 Vienna, AustriaInstitute of Applied Synthetic Chemistry, Vienna University of Technology (VUT), Getreidemarkt 9/163, A-1060 Vienna, AustriaDepartment of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna (BOKU), Konrad Lorenz Str. 24, 3430 Tulln, AustriaCenter for Analytical Chemistry, Department for Agrobiotechnology (IFA-Tulln), University of Natural Resources and Life Sciences, Vienna (BOKU), Konrad Lorenz Str. 20, 3430 Tulln, AustriaInstitute of Applied Synthetic Chemistry, Vienna University of Technology (VUT), Getreidemarkt 9/163, A-1060 Vienna, AustriaInstitute of Applied Synthetic Chemistry, Vienna University of Technology (VUT), Getreidemarkt 9/163, A-1060 Vienna, AustriaThe development of a reliable procedure for the synthesis of the 16-glucoside and 16-sulfate of the resorcylic acid lactone (RAL) type compound zearalenone is presented. Different protective group strategies were considered and applied to enable the preparation of glucosides and sulfates that are difficult to access up to now. Acetyl and p-methoxybenzyl protection led to undesired results and were shown to be inappropriate. Finally, triisopropylsilyl-protected zearalenone was successfully used as intermediate for the first synthesis of the corresponding mycotoxin glucoside and sulfate that are highly valuable as reference materials for further studies in the emerging field of masked mycotoxins. Furthermore, high stability was observed for aryl sulfates prepared as tetrabutylammonium salts. Overall, these findings should be applicable for the synthesis of similar RAL type and natural product conjugates.https://doi.org/10.3762/bjoc.10.112glycosylationmasked mycotoxinsresorcylic acid esterssulfationzearalenone |
| spellingShingle | Hannes Mikula Julia Weber Dennis Svatunek Philipp Skrinjar Gerhard Adam Rudolf Krska Christian Hametner Johannes Fröhlich Synthesis of zearalenone-16-β,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation Beilstein Journal of Organic Chemistry glycosylation masked mycotoxins resorcylic acid esters sulfation zearalenone |
| title | Synthesis of zearalenone-16-β,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation |
| title_full | Synthesis of zearalenone-16-β,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation |
| title_fullStr | Synthesis of zearalenone-16-β,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation |
| title_full_unstemmed | Synthesis of zearalenone-16-β,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation |
| title_short | Synthesis of zearalenone-16-β,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation |
| title_sort | synthesis of zearalenone 16 β d glucoside and zearalenone 16 sulfate a tale of protecting resorcylic acid lactones for regiocontrolled conjugation |
| topic | glycosylation masked mycotoxins resorcylic acid esters sulfation zearalenone |
| url | https://doi.org/10.3762/bjoc.10.112 |
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