Lateral protonation of a glycosidase inhibitor. Structure of the Bacillus agaradhaerens Cel5A in complex with a cellobiose-derived imidazole at 0.97 Å resolution [13]

Journal of the American Chemical Society

Volumn 121, Issue 11, 1999, Pages 2621-2622

  Varrot, Annabelle ^a   Schülein, Martin ^b   Pipelier, Muriel ^c   Vasella, Andrea ^c   Davies, Gideon J ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b NOVO NORDISK A S   (Denmark)

^c ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CELLOBIOSE; GLYCOSIDASE INHIBITOR; IMIDAZOLE DERIVATIVE;

BACILLUS; CRYSTAL STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME MECHANISM; ENZYME STRUCTURE; ENZYME SUBSTRATE COMPLEX; LETTER; NONHUMAN; PROTON TRANSPORT; SYNTHESIS;

EID: 0033599494     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984238n     Document Type: Letter

References (35)

1. Legler, G. Adv. Carbohyd. Chem. Biochem. 1990, 48, 319-385.
2. von Itzstein, M.; Colman, P. Curr. Opin. Struct. Biol 1996, 6, 703-709.
3. Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 5, 605-611.
4. Henrissat, B.; Bairoch, A. Biochem. J. 1996, 316, 695-696.
5. Davies, G.; Henrissat, B. Structure 1995, 3, 853-859.
6. Henrissat, B.; Davies, G. J. Curr. Opin. Struct. Biol. 1997, 7, 637-644.
7. Sinnott, M. L. Glycosyl group transfer. In Enzyme Mechanisms; Page, M. I., Williams, A., Eds.; Royal Society of Chemistry: London, 1987; pp 259-297.
8. Davies, G.; Sinnott, M. L.; Withers, S. G. Glycosyl Transfer. In Comprehensive Biological Catalysis; Sinnott, M. L., Ed.; Academic Press: London, 1997; Vol. 1, pp 119-209.
9. Koshland, D. E. Biol. Rev. 1953, 28, 416-436.
10. Heightman, T. D.; Locatelli, M.; Vasella, A. Helv. Chim. Acta 1996, 79, 2190-2200.
11. Heightman, T.; Vasella, A. Angew. Chem. In press.
12. Henrissat, B.; Callebaut, I.; Fabrega, S.; Lehn, P.; Mornon, J.-P.; Davies, G. P.N.A.S. (USA) 1995, 92, 7090-7094.
13. Terwisscha van Scheltinga, A. C.; Armand, S.; Kalk, K. H.; Isogai, A.; Henrissat, B.; Dijkstra, B. W. Biochemistry 1995, 34, 15619-15623.
14. Tews, I.; Perrakis, A.; Oppenheim, A.; Dauter, Z.; Wilson, K. S.; Vorgias, C. E. Nat. Struct. Biol. 1996, 3, 638-648.
15. Sulzenbacher, G.; Driguez, H.; Henrissat, B.; Schülein, M.; Davies, G. J. Biochemistry 1996, 35, 15280-15287.
16. Törrönen, A.; Harkki, A.; Rouvinen, J. EMBO J. 1994, 13, 2493-2501.
17. Sulzenbacher, G.; Shareck, F.; Morosoli, R.; Dupont, C.; Davies, G. J. Biochemistry 1997, 36, 16032-16039.
18. Strynadka, N. C. J.; James, M. N. G. J. Mol. Biol. 1991, 220, 401-424.
19. Weaver, L. H.; Gruwreath producttter, M. G.; Matthews, B. W. J. Mol. Biol. 1995, 245, 54-68.
20. Kuroki, R.; Weaver, L. H.; Matthews, B. W. Science 1993, 262, 2030-2033.
21. Davies, G. J.; Tolley, S. P.; Henrissat, B.; Hjort, C.; Schülein, M. Biochemistry 1995, 34, 16210-16220.
22. Piens, K.; Pipelier, M.; Vonhoff, S.; Vasellu, A. Helv. Chim. Acta. In press.
23. Granier, T.; Panday, N.; Vasella, A. Helv. Chim. Acta, 1997, 80, 979-987.
24. Tatsuta, K.; Ikeda, Y.; Miura, S. J. Antibiot. 1996, 49, 836-838.
25. Tatsuta, K.; Miura, S.; Ohta, S.; Gunji, H. Tetrahedron Lett. 1995, 36, 1085-1088.
26. Tatsuta, K.; Miura, S.; Ohta, S.; Gunji, H. J. Antibiot. 1995, 48, 286-288.
27. Heightman, T. D.; Vasella, A.; Tsitsanou, K. E.; Zographos, S. E.; Skamnaki, V. T.; Oikonomakos, N. Helv. Chim. Acta 1998, 81, 853-864.
28. Davies, G. J.; Dauter, M.; Brzozowski, A. M.; Bjornvad, M. E.; Anderson, K. V.; Schülein, M. Biochemistry 1998, 37, 1926-1932.
29. Davies, G. J.; Mackenzie, L.; Varrot, A.; Dauter, M.; Brzozowski, A. M.; Schülein, M.; Withers, S. G. Biochemistry 1998, 37, 11707-11713.
30. Emmert, P.; Vasella, A.; Weber, M.; Rupitz, K.; Withers, S. G. Carbohydr. Res. 1993, 250, 113-128.
31. a value of the glucose-derived imidazole is 6.1 (Panday, N.; Vasella, A., in preparation).
32. a value of the glucose-derived imidazole is 6.1 (Panday, N.; Vasella, A., in preparation).
33. free = 0.12, and coordinates have been deposited with the Brookhaven Protein Databank under accession code 8A3H.
34. free = 0.12, and coordinates have been deposited with the Brookhaven Protein Databank under accession code 8A3H.
35. Raymond, S.; Henrissat, B.; Qui, D. T.; Kvick, A.; Chanzy, H. Carbohydr. Res. 1995, 277, 209-229.