Journal
WORLD MYCOTOXIN JOURNAL
Volume 5, Issue 3, Pages 289-296Publisher
WAGENINGEN ACADEMIC PUBLISHERS
DOI: 10.3920/WMJ2012.1404
Keywords
mycotoxin conjugate; biomarker; synthesis; phase II metabolite; glucuronidation; ZEA-14-GlcA
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Funding
- Austrian Science Fund (FWF) [L255-B11]
- EC [KBBE-2007-22269-2 MYCORED]
- Federal Ministry of Economy, Family and Youth
- National Foundation for Research, Technology and Development
- graduate school program Applied Bioscience Technology of the Vienna University of Technology
- University of Natural Resources and Life Sciences Vienna
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The Fusarium mycotoxin zearalenone (ZEA) is mainly converted to the conjugate zearalenone-14-beta,D-glucuronide (ZEA-14-GlcA) during phase II detoxification in humans and animals. This metabolite - previously described as zearalenone-4-O-beta, D-glucuronide - is excreted via urine and could therefore serve as possible biomarker for ZEA exposure to estimate its intake. Direct determination of this substance is limited by the availability of a reference substance. So far, only the production of small amounts by enzymatic synthesis has been described. In this work, a fast and reproducible protocol for the chemical synthesis of ZEA-14-GlcA was developed, using substituted beta-resorcylic acid esters as mycotoxin mimics and different glucuronyl donors for optimising the glycosylation (Konigs-Knorr, trifluoroacetimidate method) and the deprotection step. This cost-effective procedure should be easily reproducible in other labs using standard equipment and common reagents.
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