Straightforward chemo-enzymatic synthesis of new aminocyclitols, analogues of valiolamine and their evaluation as glycosidase inhibitors

Tetrahedron Asymmetry

Volumn 17, Issue 18, 2006, Pages 2684-2688

  El Blidi, Lahssen ^a   Ahbala, Mustapha ^b   Bolte, Jean ^a   Lemaire, Marielle ^a  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

^b FACULTÉ DES SCIENCES   (Morocco)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXYMETHYL 6 NITROCYCLOHEXANE 1,2,3,5 TETRAOL; 6 AMINO 1 HYDROXYMETHYLCYCLOHEXANE 1,2,3,5 TETRAOL; ACETAL; ALDEHYDE DERIVATIVE; AMINOCYCLITOL; BUTYRALDEHYDE; DIHYDROXYACETONE PHOSPHATE; FRUCTOSE BISPHOSPHATE ALDOLASE; GLYCOSIDASE; GLYCOSIDASE INHIBITOR; HYDROXYL GROUP; KETONE DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; VALIOLAMINE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; DRUG SYNTHESIS; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY;

EID: 33750526647     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.09.010     Document Type: Article

References (26)

1. Kobata A. Anal. Biochem. 100 (1979) 1-14
2. Lehmann J. Carbohydrates: Structure and Biology (1998), G. Thieme, Verlag, New York
3. Melendez-Hevia E., Waddell T.G., and Shelton E.D. Biochem. J. 295 (1993) 477-483
4. Sharon N., and Lis H. Sci. Am. 268 (1993) 82-89
5. Sharon N., and Lis H. Science 246 (1989) 227-234
6. Kornfeld R., and Kornfeld S. Annu. Rev. Biochem. 45 (1976) 217-237
7. Kang M.S., Liu P.S., Bernotas R.C., Harry B.S., and Sunkara P.S. Glycobiology 5 (1995) 147-152
8. Varki, A., Cummings, R., Esko, J., Freeze, H., Hart, G., Marth, J., Eds.; Cold Spring Harbor Laboratory Press, Woodbury, New York, 1999.
9. Herscovics A. Biochim. Biophys. Acta 1473 (1999) 96-107
10. For a review, see:. Asano N. Glycobiology 13 (2003) 93R
11. Scheen A.J. Drugs 63 (2003) 933-951
12. Ratner L., Heyden N.V., and Dedera D. Virology 181 (1991) 180-192
13. Mehta A., Rudd P.M., Block T.M., and Dwek R.A. Biochem. Soc. Trans. 25 (1997) 1188-1193
14. Goss P.E., Baker M.A., Carver J.P., and Dennis J.W. Clin. Cancer Res. 1 (1995) 935-944
15. Nishimura Y., Satoh T., Adachi H., Kondo S., Takeuchi T., Azetaka M., Fukuyasu H., and Lizuka Y. J. Med. Chem. 40 (1997) 2626-2633
16. Lillelund V.H., Jensen H.H., Liang X., and Bols M. Chem. Rev. 102 (2002) 515-553
17. Chen X., Fan Y., Zheng Y., and Shen Y. Chem. Rev. 103 (2003) 1955-1978
18. Ogawa S., Ohishi Y., Asada M., Tomoda A., Takahashi A., Ooki Y., Mori M., Itoh M., and Korenaga T. Org. Biomol. Chem. 3 (2004) 884-889
19. Ogawa S. In: Chapleur Y. (Ed). Carbohydrate Mimics (1998), Wiley-VCH, Weinheim, Germany 88-106
20. El Blidi L., Crestia D., Gallienne E., Demuynck C., Bolte J., and Lemaire M. Tetrahedron: Asymmetry 15 (2004) 2951-2954
21. Trost B.M., Dumas J., and Villa M. J. Am. Chem. Soc. 114 (1992) 9836-9845
22. Hoaglin R.I., Kubler D.G., and Montagna A.E. J. Am. Chem. Soc. 80 (1958) 5460-5463
23. Yanovskaya L.A., Kucherov V.F., and Kovalev B.G. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) (1962) 623-629
24. Charmantray F., El Blidi L., Gefflaut T., Hecquet L., Bolte J., and Lemaire M. J. Org. Chem. 69 (2004) 9310-9313
25. Bergmeyer H.U. Methods in Enzymatic Analysis. 34th ed. Vol. 11 (1984), Chemie pp 146-147
26. Sorgedrager M.J., Malpique R., van Rantwijk F., and Sheldon R.A. Tetrahedron: Asymmetry 15 (2004) 1295-1299