The synthesis and enzymic hydrolysis of (E)-2-[2,3-2H2]propenyl glucosinolate: Confirmation of the rearrangement of the thiohydroximate moiety

Rossiter, J. T., Pickett, J. A. ORCID: https://orcid.org/0000-0002-8386-3770, Bennett, J. M., Bones, A. M., Powell, J. and Cobb, J. 2007. The synthesis and enzymic hydrolysis of (E)-2-[2,3-2H2]propenyl glucosinolate: Confirmation of the rearrangement of the thiohydroximate moiety. Phytochemistry 68 (10) , pp. 1384-1390. 10.1016/j.phytochem.2007.02.030

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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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Publisher:	Elsevier
ISSN:	0031-9422
Last Modified:	18 Feb 2026 16:21
URI:	https://orca.cardiff.ac.uk/id/eprint/185001

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