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

Phytochemistry

Volumn 68, Issue 10, 2007, Pages 1384-1390

  Rossiter, J T ^a   Pickett, J A ^b   Bennett, M H ^a   Bones, A M ^c   Powell, G ^a   Cobb, J ^d  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b ROTHAMSTED RESEARCH   (United Kingdom)

^c NORWEGIAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Norway)

^d KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

Deuterium NMR spectroscopy; Glucosinolate; Isothiocyanate; Isotope; Mechanism; Sinigrin; Synthesis; Thiocyanate

Indexed keywords

2 (2,3 2H2)PROPENYL GLUCOSINOLATE; 2-(2,3-2H2)PROPENYL GLUCOSINOLATE; DEUTERIUM; GLUCOSINOLATE; ISOTHIOCYANIC ACID; ISOTHIOCYANIC ACID DERIVATIVE; OXIME; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

CATALYSIS; DEUTERIUM; GLUCOSINOLATES; HYDROLYSIS; ISOTHIOCYANATES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXIMES;

EID: 34247582937     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2007.02.030     Document Type: Article

References (23)

1. Abramski W., and Chmielewski M. Practical synthesis of sinigrin. Journal of Carbohydrate Chemistry 15 (1996) 109-113
2. Ballini R., Barboni L., and Giarlo G. The first conversion of primary alkyl halides to nitroalkanes under aqueous medium. Journal of Organic Chemistry 69 (2004) 6907-6908
3. Benn M.H., and Ettlinger M.G. The synthesis of sinigrin. Journal of the Chemical Society, Chemical Communications (London) (1965) 445-447
4. Bones A.M., and Rossiter J.T. The myrosinase-glucosinolate system, its organization and biochemistry. Physiologia Plantarum 97 (1996) 194-208
5. Bones A.M., and Rossiter J.T. The enzymic and chemically induced decomposition of glucosinolates. Phytochemistry 67 (2006) 1053-1067 (Epub 2006, April 1019)
6. Bourderioux A., Lefoix M., Gueyrard D., Tatibouet A., Cottaz S., Arzt S., Burmeister W.P., and Rollin P. The glucosinolate-myrosinase system. New insights into enzyme-substrate interactions by use of simplified inhibitors. Organic & Biomolecular Chemistry 3 (2005) 1872-1879
7. Burow M., Bergner A., Gershenzon J., and Wittstock U. Glucosinolate hydrolysis in Lepidium Sativum-identification of the thiocyanate-forming protein. Plant Mol Biol 63 (2007) 49-61 (Epub 2006 December 2001)
8. Chen S.X., and Halkier B.A. In vivo synthesis and purification of radioactive p-hydroxybenzylglucosinolate in Sinapis alba L. Phytochemical Analysis 11 (2000) 174-178
9. Chevolleau S., Joseph B., Rollin P., and Tulliez J. Synthesis of [H-3] labeled glucobrassicin, a potential radiotracer for metabolic studies of indole glucosinolates. Journal of Labelled Compounds & Radiopharmaceuticals 33 (1993) 671-679
10. Fahey J.W., Zalcmann A.T., and Talalay P. The chemical diversity and distribution of glucosinolates and isothiocyanates among plants (vol. 56, p. 5, 2001). Phytochemistry 59 (2002) 237
11. Foo, H.L., 1998. Purification and characterisation of myrosinase and epithiospecifier protein from cruciferous plants. PhD, University of London, London.
12. Foo H.L., Gronning L.M., Goodenough L., Bones A.M., Danielsen B., Whiting D.A., and Rossiter J.T. Purification and characterisation of epithiospecifier protein from Brassica napus: enzymic intramolecular sulphur addition within alkenyl thiohydroximates derived from alkenyl glucosinolate hydrolysis. FEBS Letters 468 (2000) 243-246
13. Grubb C.D., and Abel S. Glucosinolate metabolism and its control. Trends in Plant Science 11 (2006) 89-100
14. Halkier B.A., and Gershenzon J. Biology and biochemistry of glucosinolates. Annual Review of Plant Biology 57 (2006) 303-333
15. Holst B., and Williamson G. A critical review of the bioavailability of glucosinolates and related compounds. Natural Product Reports 21 (2004) 425-447
16. Kliebenstein D.J., Kroymann J., and Mitchell-Olds T. The glucosinolate-myrosinase system in an ecological and evolutionary context. Current Opinion in Plant Biology 8 (2005) 264-271
17. Kornblum N., Larson H.O., Blackwood R.K., Mooberry D.D., Oliveto E.P., and Graham G.E. Chemistry of aliphatic and alicyclic nitro compounds. XII. A new method for the synthesis of aliphatic nitro compounds. Journal of the American Chemical Society 78 (1956) 1497-1501
18. Lambrix V., Reichelt M., Mitchell-Olds T., Kliebenstein D.J., and Gershenzon J. The Arabidopsis epithiospecifier protein promotes the hydrolysis of glucosinolates to nitriles and influences Trichoplusia ni herbivory. Plant Cell 13 (2001) 2793-2807
19. Luthy J., and Benn M.H. Thiocyanate formation from glucosinolates: a study of the autolysis of allylglucosinolate in Thlaspi arvense L. seed flour extracts. Canadian Journal of Biochemistry 55 (1977) 1028-1031
20. 5]gluconasturtiin and its metabolites for metabolic studies. Journal of Labelled Compounds & Radiopharmaceuticals 48 (2005) 897-907
21. Rossiter J.T., and James D.C. Biosynthesis of (R)-2-hydroxybut-3-enylglucosinolate (progoitrin) from [3,4-3H]but-3-enylglucosinolate in Brassica napus. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry 1972-1999 (1990) 1909-1913
22. Svanem P.-J., Bones A.M., and Rossiter J.T. Metabolism of [a-14C]-desulfophenethylglucosinolate in Nasturtium officinale. Phytochemistry 44 (1997) 1251-1255
23. Zhang Z.Y., Ober J.A., and Kliebenstein D.J. The gene controlling the quantitative trait locus EPITHIOSPECIFIER MODIFIER1 alters glucosinolate hydrolysis and insect resistance in Arabidopsis. Plant Cell 18 (2006) 1524-1536