The synthesis and enzymic hydrolysis of (E)-2-[2,3-2H2]propenyl glucosinolate: confirmation of the rearrangement of the thiohydroximate moiety.
(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.
Rossiter
J T
JT
Division of Biology, Imperial College London, Wye Campus, Wye, Ashford, Kent TN25 5AH, UK. j.rossiter@imperial.ac.uk
Pickett
J A
JA
Bennett
M H
MH
Bones
A M
AM
Powell
G
G
Cobb
J
J
D002384:Catalysis; D003903:Deuterium; D005961:Glucosinolates / Q000138:chemical synthesis* / Q000737:chemistry; D006868:Hydrolysis; D017879:Isothiocyanates / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010091:Oximes / Q000737:chemistry
C521577:2-(2,3-2H2)propenyl glucosinolate; D005961:Glucosinolates; D017879:Isothiocyanates; D010091:Oximes; C037152:isothiocyanic acid; D003903:Deuterium