Synthetic routes to isotopologues of acetylated derivatives of deoxynivalenol to be used in stable isotope dilution assays

Abstract

The isomers 3-O-acetyl- and 15-O-acetyldeoxynivalenol (3-ADON and 15-ADON) are intermediates of deoxynivalenol (DON) biosynthesis. Both compounds are present along with DON in contaminated food and feed, but they are not analysed routinely. This review describes synthetic routes to stable isotope labelled 3-ADON and 15-ADON that can be used as internal standards in stable isotope dilution assays. The label was introduced either as [2H3]-acetyl or [13C2]-acetyl group in all protocols. Regioselective acetylation can be obtained by the use of protection groups or stepwise acetylation and hydrolysis. Advantages and disadvantages of both strategies are discussed.