Biochemical and Structural Assessment of the 1-N-Azasugar GalNAc-isofagomine as a Potent Family 20 β-N-Acetylhexosaminidase Inhibitor

Journal of Biological Chemistry

Volumn 276, Issue 45, 2001, Pages 42131-42137

  Mark, Brian L ^a   Vocadlo, David J ^b   Zhao, Dalian ^c   Knapp, Spencer ^c   Withers, Stephen G ^b   James, Michael N G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^c RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITION; ENZYMES; NITROGEN; ORGANIC COMPOUNDS; PROTONS;

CATALYTIC RESIDUES;

BIOCHEMISTRY;

AZASUGAR; BETA N ACETYLHEXOSAMINIDASE; BETA N ACETYLHEXOSAMINIDASE INHIBITOR; CARBOXYLIC ACID; ENZYME INHIBITOR; GLYCOSIDASE; HETEROCYCLIC COMPOUND; ISOFAGOMINE; N ACETYLGALACTOSAMINE; N ACETYLGALACTOSAMINE ISOFAGOMINE; NITROGEN; PROTON; SUGAR; UNCLASSIFIED DRUG; IMINOSUGAR; PIPERIDINE DERIVATIVE;

ARTICLE; ELECTRICITY; ENZYME INHIBITION; ENZYME MECHANISM; PRIORITY JOURNAL; PROTEIN FAMILY; STREPTOMYCES; STREPTOMYCES PLICATUS; SYNTHESIS; CHEMISTRY; DRUG ANTAGONISM; ENZYMOLOGY; HYDROGEN BOND;

SPHEX; STREPTOMYCES; STREPTOMYCES PLICATUS;

BETA-N-ACETYLHEXOSAMINIDASE; ENZYME INHIBITORS; HYDROGEN BONDING; IMINO PYRANOSES; PIPERIDINES; STREPTOMYCES;

EID: 0035834783     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.M107154200     Document Type: Article

References (38)

1. Heightman, T. D., and Vasella, A. T. (1999) Angew. Chem. Int. Ed. Engl. 38, 750-770
2. Gubareva, L. V., Kaiser, L., and Hayden, F. G. (2000) Lancet 355, 827-835
3. Taylor, G. (1996) Curr. Opin. Struct. Biol. 6, 830-837
4. Martin, A. E., and Montgomery, P. A. (1996) Am. J. Health Syst. Pharm. 53, 2277-2290
5. Welborn, T. A. (1998) Med. J. Aust. 168, 76-78
6. Sinnott, M. L. (1990) Chem. Rev. 90, 1171-1202
7. McCarter, J. D., and Withers, S. G. (1994) Curr. Opin. Struct. Biol. 4, 885-892
8. Henrissat, B. (1991) Biochem. J. 280, 309-316
9. Henrissat, B., and Davies, G. (1997) Curr. Opin. Struct. Biol. 7, 637-644
10. Henrissat, B., and Bairoch, A. (1996) Biochem. J. 316, 695-696
11. Davies, G., and Henrissat, B. (1995) Structure 3, 853-859
12. Tews, I., Perrakis, A., Oppenheim, A., Dauter, Z., Wilson, K. S., and Vorgias, C. E. (1996) Nat. Struct. Biol. 3, 638-648
13. Tews, I., Terwisscha van Scheltinga, A. C., Perrakis, A., Wilson, K. S., and Dijkstra, B. W. (1997) J. Am. Chem. Soc. 119, 7954-7959
14. Mark, B. L., Wasney, G. A., Salo, T. J., Khan, A. R., Cao, Z., Robbins, P. W., James, M. N., and Triggs-Raine, B. L. (1998) J. Biol. Chem. 273, 19618-19624
15. Drouillard, S., Armand, S., Davies, G. J., Vorgias, C. E., and Henrissat, B. (1997) Biochem. J. 328, 945-949
16. Sulzenbacher, G., Driguez, H., Heririssat, B., Schulein, M., and Davies, G. J. (1996) Biochemistry 35, 15280-15287
17. Knapp, S., Vocadlo, D., Gao, Z., Kirk, B., Lou, J., and Withers, S. G. (1996) J. Am. Chem. Soc. 118, 6804-6805
18. Mark, B. L., Vocadlo, D. J., Knapp, S., Triggs-Raine, B. L., Withers, S. G., and James, M. N. G. (2001) J. Biol. Chem. 276, 10330-10337
19. McCarter, J. D., Adam, M. J., and Withers, S. G. (1992) Biochem. J. 286, 721-727
20. Namchuk, M. N., and Withers, S. G. (1995) Biochemistry 34, 16194-16202
21. Bols, M. (1998) Acc. Chem. Res. 31, 1-8
22. Ichikawa, Y., Igarashi, Y., Ichikawa, M., and Suhara, Y. (1998) J. Am. Chem. Soc. 120, 5854-5854
23. Notenboom, V., Williams, S. J., Hoos, R., Withers, S. G., and Rose, D. R. (2000) Biochemistry 39, 11553-11563
24. Uitdehaag, J. C. M., Mosi, R., Kalk, K. H., van der Veen, B. A., Dijkhuizen, L., Withers, S. G., and Dijkstra, B. W. (1999) Nat. Struct. Biol. 6, 432-436
25. Liu, H., Liang, X., Shoel, H., Blow, A., and Bols, M. (2001) J. Am. Chem. Soc. 123, 5116-5117
26. Knapp, S., and Zhao, D. (2000) Org. Lett. 2, 4037-4040
27. Leatherbarrow, R. J. (1998) GraFit, version 4.0., Erithacus Software, Ltd., Horley Surrey, UK
28. Otwinowski, Z., and Minor, W. (1997) Methods Enzymol. 276, 307-326
29. Brunger, A. T., Adams, P. D., Clore, G. M., DeLano, W. L., Gros, P., Grosse-Kunstleve, R. W., Jiang, J. S., Kuszewski, J., Nilges, M., Pannu, N. S., Read, R. J., Rice, L. M., Simonson, T., and Warren, G. L. (1998) Acta Crystallogr. Sect. D Biol. Crystallogr. 54, 905-921
30. Jones, T. A., Zou, J. Y., Cowan, S. W., and Kjeldgaard. (1991) Acta Crystallogr. Sect. A 47, 110-119
31. Kleywegt, G. J. (1995) CCP4/ESF-EACBM Newsletter on Protein Crystallography 31, 45-50
32. Gilardi, R. D., and Flippen, J. L. (1974) Acta Crystallogr. Sect. B Struct. Sci. 30, 2931-2933
33. White, A., Tull, D., Johns, K., Withers, S. G., and Rose, D. R. (1996) Nat. Struct. Biol. 3, 149-154
34. Mo, F., and Jensen, L. H. (1978) Acta Crystallogr. Sect. B Struct. Sci. 34, 1562-1569
35. Nishimura, Y., Satoh, T., Kudo, T., Kondo, S., and Takeuchi, T. (1996) Bioorg. Med. Chem. 4, 91-96
36. Laskowski, R. A., MacArthur, M. W., Moss, D. S., and Thornton, J. M. (1993) J. Appl. Crystallogr. 26, 283-291
37. Davies, G. J., Mackenzie, L., Varrot, A., Dauter, M., Brzozowski, A. M., Schulein, M., and Withers, S. G. (1998) Biochemistry 37, 11707-11713
38. Vocadlo, D. J., Mayer, C., He, S., and Withers, S. G. (2000) Biochemistry 39, 117-126