The synthesis and enzymic hydrolysis of (E)-2-[2,3-2H2]propenyl glucosinolate: confirmation of the rearrangement of the thiohydroximate moiety |
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| Authors: | Rossiter J T Pickett J A Bennett M H Bones A M Powell G Cobb J |
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| Institution: | Division of Biology, Imperial College London, Wye Campus, Wye, Ashford, Kent TN25 5AH, UK. j.rossiter@imperial.ac.uk |
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| Abstract: | (E)-2-2,3-2H2]propenyl glucosinolate was synthesised starting from (E)-3,4-2H2]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)-2-2,3-2H2]propenyl glucosinolate was completed via the nitro intermediate to form the basic desulphoglucosinolate skeleton. The (E)-2-2,3-2H2]propenyl glucosinolate was fully characterised and deuterium NMR spectroscopy used to examine the rearrangement of the thiohydroximate to the isothiocyanate and thiocyanate. |
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| Keywords: | Glucosinolate Sinigrin Thiocyanate Isothiocyanate Synthesis Isotope Mechanism Deuterium NMR spectroscopy |
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