Sulfation of deoxynivalenol, its acetylated derivatives, and T2-toxin

Philipp Fruhmann; Philipp Skrinjar; Julia Weber; Hannes Mikula; Benedikt Warth; Michael Sulyok; Rudolf Krska; Gerhard Adam; Erwin Rosenberg; Christian Hametner; Johannes Fröhlich

doi:10.1016/j.tet.2014.05.064

Sulfation of deoxynivalenol, its acetylated derivatives, and T2-toxin

Tetrahedron. 2014 Aug 26;70(34):5260-5266. doi: 10.1016/j.tet.2014.05.064.

Affiliations

¹ Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, A-1060 Vienna, Austria.
² University of Natural Resources and Life Sciences, Vienna (BOKU), Dept. for Agrarbiotechnology (IFA-Tulln), Center for Analytical Chemistry, Konrad Lorenz Str. 20, A-3430 Tulln, Austria.
³ University of Natural Resources and Life Sciences, Vienna (BOKU), Dept. of Applied Genetics and Cell Biology, Konrad Lorenz Str. 20, A-3430 Tulln, Austria.
⁴ Institute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164, A-1060 Vienna, Austria.

Abstract

The synthesis of several sulfates of trichothecene mycotoxins is presented. Deoxynivalenol (DON) and its acetylated derivatives were synthesized from 3-acetyldeoxynivalenol (3ADON) and used as substrate for sulfation in order to reach a series of five different DON-based sulfates as well as T2-toxin-3-sulfate. These substances are suspected to be formed during phase-II metabolism in plants and humans. The sulfation was performed using a sulfuryl imidazolium salt, which was synthesized prior to use. All protected intermediates and final products were characterized via NMR and will serve as reference materials for further investigations in the fields of toxicology and bioanalytics of mycotoxins.

Keywords: Deoxynivalenol; Masked mycotoxins; Sulfation; T2-toxin; Trichothecenes.