The synthesis and enzymic hydrolysis of ( E)-2-[2,3- 2H 2]propenyl glucosinolate: Confirmation of the rearrangement of the thiohydroximate moiety

( E)-2-[2,3- 2H 2]propenyl glucosinolate was synthesised and fully characterized in terms of its structure and enzymic degradation. The rearrangement of the aglycone was examined by deuterium NMR spectroscopy. ( E)-2-[2,3- 2H 2]propenyl glucosinolate was synthesised starting from ( E)-[3,4- 2H 2]but-3-en-1-ol, which was produced by reduction of but-3-yn-1-ol with deuterium gas in the presence of Lindlar’s catalyst. The synthesis of ( E)-2-[2,3- 2H 2]propenyl glucosinolate was completed via the nitro intermediate to form the basic desulphoglucosinolate skeleton. The ( E)-2-[2,3- 2H 2]propenyl glucosinolate was fully characterised and deuterium NMR spectroscopy used to examine the rearrangement of the thiohydroximate to the isothiocyanate and thiocyanate.