A simple O-sulfated thiohydroximate molecule to be the first micromolar range myrosinase inhibitor

Tetrahedron Letters

Volumn 50, Issue 26, 2009, Pages 3302-3305

  Cerniauskaite, Deimante ^a,b   Gallienne, Estelle ^a   Karciauskaite, Henreta ^b   Farinha, Andrea S F ^a   Rousseau, Jolanta ^b   Armand, Sylvie ^c   Tatibouët, Arnaud ^a   Sackus, Algirdas ^b   Rollin, Patrick ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b KAUNAS UNIVERSITY OF TECHNOLOGY   (Lithuania)

^c CENTRE DE RECHERCHES SUR LES MACROMOLÉCULES VÉGÉTALES CERMAV CNRS   (France)

Author keywords

Glucosinolate; Myrosinase inhibition; Sulfation; Thiohydroximate

Indexed keywords

AGLYCONE; AMMONIUM DERIVATIVE; CYSTEAMINE DERIVATIVE; ENZYME INHIBITOR; GLUCOSINOLATE; PHENOTHIAZINE; THIOGLUCOSIDASE; THIOHYDROXIMATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENZYME INHIBITION; IC 50; INHIBITION KINETICS; MOLECULE; SULFATION;

EID: 65549097247     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.072     Document Type: Article

References (28)

1. Fahey J.W., Zalcmann A.T., and Talalay P. Phytochemistry 56 (2001) 5-51
2. Hayes J.D., Kelleher M.O., and Eggleston I.M. Eur. J. Nutr. 47 (2008) 73-88
3. Morant A.V., Jørgensen K., Jørgensen C., Paquette S.M., Sánchez-Pérez R., Møller N.L., and Bak S. Phytochemistry 69 (2008) 1795-1813
4. Iori R., Rollin P., Streicher H., Thiem J., and Palmieri S. FEBS Lett. 385 (1996) 87-90
5. Cottaz S., Henrissat B., and Driguez H. Biochemistry 35 (1996) 15256-15259
6. Blanc-Muesser M., Driguez H., Joseph B., Viaud M.C., and Rollin P. Tetrahedron Lett. 31 (1990) 3867-3868
7. Gardrat C., Quinsac A., Joseph B., and Rollin P. Heterocycles 35 (1996) 1015-1027
8. Joseph B., and Rollin P. J. Carbohydr. Chem. 12 (1993) 719-729
9. Cottaz S., Rollin P., and Driguez H. Carbohydr. Res. 298 (1997) 127-130
10. Kjaer A., and Skrydstrup T. Acta Chem. Scand. 41 (1987) 29-33
11. Aucagne V., Gueyrard D., Tatibouët A., Quinsac A., and Rollin P. Tetrahedron 56 (2000) 2647-2654
12. Lazar S., and Rollin P. Tetrahedron Lett. 35 (1994) 2173-2174
13. Mays J.R., Weller R.L., Sami Sarfaraz R., Mukhtar H., and Rajski S.R. ChemBioChem 9 (2008) 729-747
14. Official method ISO-9167-1. EEC Regulation No. 1864/90, Enclosure VIII. Offic. J. Eur. Commun. L170 (1990) 27-34
15. Wathelet J.-P., Iori R., Leoni O., Rollin P., Quinsac A., and Palmieri S. Agroindustria 3 (2004) 257-266
16. Bourderioux A., Lefoix M., Gueyrard D., Tatibouët A., Cottaz S., Arzt S., Burmeister W.P., and Rollin P. Org. Biomol. Chem 3 (2005) 1872-1879
17. Kumaran G., and Kulkarni G.H. Tetrahedron Lett. 35 (1994) 9099-9100
18. Kumaran G., and Kulkarni G.H. J. Org. Chem. 62 (1997) 1516-1520
19. Liu K.C., Shelton B.R., and Howe R.K. J. Org. Chem. 45 (1980) 3916
20. Fujiwara A.N., Acton E.M., and Goodman L. J. Heterocycl. Chem. 10 (1967) 126-127
21. Winchester M.J., and Popp F.D. J. Heterocycl. Chem. 12 (1975) 547-549
22. Luzzio F.A. Tetrahedron 57 (2001) 915-945
23. Davidson N.E., Rutherford T.J., and Botting N.P. Carbohydr. Res. 330 (2001) 295-307
24. Cassel S., Debaig C., Benvegnu T., Chaimbault P., Lafosse M., Plusquellec D., and Rollin P. Eur. J. Org. Chem. (2001) 875-896 and references cited therein
25. +: 311.1429, found: 311.1454.
26. +: 389.0841, found: 389.0826.
27. 2S).
28. +