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Selected Publication:

Mikula, H; Weber, J; Svatunek, D; Skrinjar, P; Adam, G; Krska, R; Hametner, C; Frohlich, J.
(2014): Synthesis of zearalenone-16-beta,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation
BEILSTEIN J ORG CHEM. 2014; 10: 1129-1134. FullText FullText_BOKU

Abstract:
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.
Authors BOKU Wien:
Adam Gerhard
Krska Rudolf
Svatunek Dennis
BOKU Gendermonitor:


Find related publications in this database (Keywords)
glycosylation
masked mycotoxins
resorcylic acid esters
sulfation
zearalenone


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