182. Synthesis of fused triazoles as probes for the active site of retaining β-glycosidases: From which direction is the glycoside protonated?

Helvetica Chimica Acta

Volumn 79, Issue 8, 1996, Pages 2190-2200

  Heightman, Tom D ^a   Locatelli, Monica ^a   Vasella, Andrea ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BETA GALACTOSIDASE; BETA GLUCOSIDASE; BETA GLYCOSIDASE INHIBITOR; TETRAZOLE DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTALLOGRAPHY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME BINDING; ENZYME INHIBITION; NUCLEAR MAGNETIC RESONANCE;

EID: 0029908774     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.19960790814     Document Type: Article

References (49)

1. G. Legler, Adv. Carbohydr. Chem Biochem 1990, 48, 319.
2. M. L. Sinnott, Chem. Rev. 1990, 90, 1171.
3. R. W. Franck, Bioorg. Chem. 1991, 20, 77.
4. Y. Nishimura, Stud. Nat. Prod. Chem. 1992, 10, 495.
5. M. Sinnott, Bioorg. Chem. 1993, 21, 34.
6. G. Legler, Naturwissenschaften 1993, 80, 397.
7. G. Legler, Carbohydr. Res. 1993, 250, vii.
8. J. D. McCarter, S. G. Withers, Curr. Opin. Struct. Biol. 1994, 4, 885.
9. D. E. Koshland, Biol. Rev. 1953, 28, 416.
10. D. C. Phillips, Sci. Am. 1966, 215, 78.
11. G. Legler, Hoppe-Seyler's Z. Physiol. Chem 1970, 351, 25.
12. S G. Withers, K. Umezawa, Biochem. Biophys. Res. Commun. 1991, 177, 532.
13. B. Svensson, M. Søgaard, J Biotechnol. 1993, 29, 1.
14. M. L. Sinnott, in 'Enzyme Mechanisms', Eds. M. I. Page and A. Williams, Royal Society of Chemistry, London, 1987, p. 259.
15. J. Conchie, G. A. Levvy, Biochem. J. 1957, 65, 389.
16. E. T. Reese, F. W. Parrish, M. Ettlinger, Carbohydr. Res. 1971, 18, 381.
17. G. A. Levvy, S. M. Snaith, Adv. Enzymol. 1972, 36, 151.
18. T. Niwa, S. Inouye, T. Tsuruoka, Y. Koaze, T. Niida, Agric. Biol. Chem. 1970, 34, 966.
19. D. Beer, A. Vasella, Helv. Chim. Acta 1986, 69, 267.
20. P. Ermert, A. Vasella, Helv. Chim. Acta 1991, 74, 2043.
21. P. Ermert, A. Vasella, M. Weber, K. Rupitz, S. G. Withers, Carbohydr. Res 1993, 250, 113.
22. T. D. Heightman, P. Ermert, D. Klein, A. Vasella, Helv. Chim. Acta 1995, 78, 514.
23. K. Tatsuta, S. Miura, S. Ohta, H. Gunji, J. Antibiot. 1995, 48, 286.
24. I. Inouye, T. Tsuruoka, T. Niida, J. Antibiot. 1966, 19, 584.
25. T M. Jespersen, W. Dong, M. R. Seirks, T. Skrydstrup, I. Lundt, M. Bols, Angew. Chem. 1994, 106, 1858.
26. W. Dong, T. Jespersen, M. Bols, T. Skrydstrup, M. Sierks, Biochemistry 1996, 35, 2788.
27. A. Linden, R. Hoos, A Vasella, Acta Crystallogr., Sect. C: Cryst. Struct Commun. 1994, 50, 746.
28. R. Hoos, A. B. Naughton, W. Thiel, A. Vasella, W. Weber, K. Rupitz, S. G. Withers, Helv. Chim. Acta 1993, 76, 2666.
29. G. Papandreou, M. K. Tong, B. Ganem, J. Am. Chem. Soc. 1993, 115, 11682.
30. B. Ganem, G. Papandreou, J. Am. Chem. Soc. 1991, 113, 8984.
31. M. K. Tong, G. Papandreou, B Ganem, J. Am. Chem. Soc. 1990, 112, 6137.
32. J.-H Jeong, B. W. Murray, S. Takayama, C.-H Wong, J Am Chem. Soc. 1996, 118, 4227.
33. R. A. Field, A. H. Haines, E. J. T. Chrystal, Biorg. Med. Chem. Lett. 1991, 1, 667.
34. E. J. Hehre, D. S. Genghof, H. Sternlicht, C. F. Brewer, Biochemistry 1977, 16, 1780.
35. E. J. Hehre, C. F. Brewer, T. Uchiyama, P. Schlesselmann, J. Lehmann, Biochemistry 1980, 19, 3557.
36. T. Aoyama, H. Naganawa, H. Suda, K. Uotani, T. Aoyagi, T. Takeuchi, J. Antibiot. 1992, 45, 1557.
37. A. C. Terwisscha van Scheltinga, K. H. Kalk, J. J. Beintema, B. W. Dijkstra, Structure 1994, 2, 1181.
38. I. Tews, A. Perrakis, A. Oppenheim, Z. Dauter, K. S. Wilson, C. E. Vorgias, Nature Struct. Biol. 1996, 3, 638.
39. M. Suzuki, Y. Mikura, S. Terashima, Chem Pharm. Bull. 1986, 34, 1531.
40. E. Calzada, C. A. Clarke, C. Roussin-Bouchard, R. H. Wightman, J. Chem. Soc., Perkin Trans. 1 1995, 517.
41. J. G. Buchanan, A. D. Dunn, A. R. Edgar, J. Chem. Soc., Perkin Trans. 1 1975, 1191.
42. E P. Mitchell, S. G. Withers, P. Ermert, A. T. Vasella, E. F. Garman, N. G. Oikonomakos, L. N. Johnson, Biochemistry 1996, 35, 7341.
43. G. Legler, Hoppe-Seyler's Z. Physiol. Chem. 1968, 349, 767.
44. T. Barrett, C. G. Suresh, S P. Tolley, E J. Dodson, M. A. Hughes, Structure 1995, 3, 951.
45. R. H. Jacobsen, X.-J. Zhang, R. F. DuBose, B. W. Matthews, Nature (London) 1994, 369, 761.
46. C. Wiesmann, G. Beste, W. Hengstenberg, G. E. Schulz, Structure 1995, 3, 961.
47. A. White, D. Tull, K. Johns, S. G Withers, D. R. Rose, Nature Struct. Biol. 1996, 3, 149.
48. S. Jain, W B. Drendel, Z.-W. Chen, F. S. Mathews, W. S. Sly, J H. Grubb, Nature Struct. Biol. 1996, 3, 375.
49. B. Henrissat, Biochem. J. 1991, 280, 309.