Synthesis of deoxynivalenol-3-β-D-O-glucuronide for its use as biomarker for dietary deoxynivalenol exposure

Trichothecene mycotoxins are prevalent toxic secondary metabolic products of several fungal species and pose a serious threat to human and animal health. Deoxynivalenol (DON) is known to undergo rapid metabolisation after uptake. The formed glucuronides are urinary excreted and could therefore serve as possible biomarkers for daily uptake measurement. So far human exposure to the major toxin DON was estimated from dietary average intake or by measurement of the parent toxin after hydrolysis. These approaches are indirect and time-consuming. Due to the clear demand for a direct determination method and lack of an available reference substance we synthesised DON-3-O-beta-D-glucuronide. The Konigs-Knorr procedure using acetobromo-alpha-D-glucuronic acid methyl ester as glucuronyl-donor was optimised to produce the target compound in mg scale allowing subsequent characterisation via nuclear magnetic resonance and LC-MS/MS.