Cyclic guanidino-sugars with low pKa as transition-state analog inhibitors of glycosidases: Neutral instead of charged species are the active forms

Journal of the American Chemical Society

Volumn 118, Issue 18, 1996, Pages

  Jeong, Jin Hyun ^a   Murray, Brion W ^a   Takayama, Shuichi ^a   Wong, Chi Huey ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDASE; GLYCOSIDASE INHIBITOR; GUANIDINE DERIVATIVE;

ARTICLE; COFFEE; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME INHIBITOR INTERACTION; INHIBITION KINETICS; NONHUMAN; PH;

EID: 0029992305     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja951602z     Document Type: Article

References (53)

1. (a) Schramm, V. L.; Horenstein, B. A.; Kline, P. C. J. Biol. Chem. 1994, 269, 18259.
2. (b) Sinnott, M. L. Chem. Rev. 1990, 90, 1171-1202.
3. (c) Sharper, J. H.; Sharper, N. L. Curr. Opin. Struct. Biol. 1992, 2, 701.
4. (d) Withers, S. G.; Warren, R. A.; Street, I. P., Rupitz, K.; Kempton, J. B.; Abersold, R. J. J. Am. Chem. Soc 1990, 112, 5887.
5. (e) Singh, A. N.; Hester, L. S.; Raushel, F. M. J. Biol. Chem. 1987, 262, 2554.
6. (f) Bell, J. E.; Beyer, T. A.; Hill, R. L. J. Biol. Chem. 1976, 251, 3003-3013.
7. (g) Dale, M. P.; Ensley, H. E.; Kern, K.; Sastry, K. A. R.; Byers, L. D. Biochemistry 1985, 24, 3530-3539.
8. (h) Franck, R. W. Bioorg. Chem. 1992, 20, 77.
9. (i) Taylor, N. R.; von Itzstein, M. J. Med. Chem. 1994, 37, 616.
10. (a) Hodgson, J. Bio/Technology 1991, 9, 609.
11. (b) Asano, N.; Kizu, H.; Oseki, K.; Tomioka, E.; Matusi, K.; Okamoto, M.; Baba, M. J. Med. Chem. 1995, 38, 2349-2356.
12. (c) Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199-210.
13. (d) Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182-190.
14. (e) Wong, C.-H.: Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521-546.
15. (f) Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497-534.
16. (g) Carchon, H.; Bruyne, C. K. D. Carbohydr. Res. 1975, 41, 175-189.
17. (a) Bernotas, R. C.; Pezzone, M. A.; Ganem, B. Carbohydr. Res. 1987, 167, 305-311.
18. (b) Papandreou, G.; Tong, M. K.; Ganem, B. J. Am. Chem. Soc. 1993, 115, 11682-11690.
19. (c) Schedler, D. J. A.; Bowen, B. R.; Ganem, B. Tetrahedron Lett. 1994, 35, 3845.
20. (d) Ichikawa, M.; Igarashi, Y.; Ichikawa, Y. Tetrahedron Lett. 1995, 36, 1767-1770.
21. (e) Oszczapowicz, J.; Orlinski, R.; Walczynska, H. Pol. J. Chem. 1979, 53, 2531.
22. (f) Ichikawa, Y.; Isarashi, Y. Tetrahedron Lett. 1995, 36, 4585.
23. (g) Ermert, P.; Vasella, A. Helv. Chim. Acta 1991, 74, 2043
24. (a) Kajimoto, T.; Liu, K.-C.; Pederson, R. L.; Zhong, Z.; Ichikawa, Y.; Porco, J. A.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6187.
25. (b) Wang, Y.-F.; Dumas, D. P.; Wong, C.-H. Tetrahedron Lett. 1993, 34, 403.
26. (c) Dumas, D. P.; Kajimoto, T.; Liu, K. K.-C.; Wons, C.-H.; Berkowitz, D. B., Damshefsky, S. J. Bioorg. Med. Chem. Lett. 1992, 2, 33-36.
27. (d) Truscheit, E.; Frommer, W.; Junge, B.; Müller, L.; Schmidt, D. D.; Wingender, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 744.
28. (e) Schwarz, P. M.; Elbein, A. D. J. Biol. Chem. 1985, 26, 14452.
29. (f) Gruters, R. A.; Neefjes, J. J.; Termette, M.; Goede, R. E. Y. D.; Tulp, A. Nature 1987, 330, 74.
30. (g) Karpas, A.; Fleet, G. W. J.; Dwek, R. A.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Jacob, G. S.; Rademacher, T. W. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 9229.
31. (h) Lowarj, T. L.; Swtedler, S. J.; Hindsgaul, O. Carbohydr. Res. 1994, 256, 257-273.
32. (a) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 115, 11682-11690.
33. (b) Wong, C.-H.; Provencher, L.; Porco, I. A. J.; Jung, S.-H.; Wang, Y.-F.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492.
34. (c) Fotsch, C. H.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 3481-3484.
35. von Itzstein, M.; Wu, W.-Y.; Kok, G. B.; Pegg, M. S., Dyason, J. C.; Jin, B.; Phan, T. V.; Smythe, M. L.; White, H. F.; Oliver, S. W.; Colman, P. M.; Varshese, J. N.; Ryan, M.; Woods, J. M.; Bethell, R. C.; Hotham, V. J.; Cameron, J. M.; Penn, C. R. Nature 1993, 363, 418.
36. (a) Lehmann, J.; Rob, B. Liebigs. Ann. Chem. 1994, 805-809.
37. (b) Chan, A. W.-Y.; Ganem, B. Tetrahedron Lett. 1995, 36, 811-814.
38. (S) Henderson, I. A.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359.
39. (a) Holt, K. E.; Leeper, F. J.; Handa, S. J. J. Chem. Soc., Perkin Trans. I 1994, 231-234
40. (b) Brevet, L.; Mori, K. Synthesis 1992, 1007-1012.
41. (a) Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron Lett. 1991, 12, 3043-3046.
42. (b) Vänttinen, E.; Kanerva, L. T. Tetrahedron: Asymmetry 1992, 3, 1529-1532.
43. Kim, K. S.; Qian, L. Tetrahedron Lett. 1993, 34, 7677-7680.
44. Hoffman, R. E.; Christofides, J. C.; Davies, D. B.; Lawson, C. J. Carbohydr. Res. 1986, 153, 1-16.
45. Grein, F.; Deslongchamps, P. Can. J. Chem. 1992, 70, 1562-1572.
46. (a) Matsumoto, K.; Rapoport, H. J. Org. Chem. 1968, 33, 552-558.
47. (b) Houghten, R. A.; Simpson, R. A.; Hanson, R. N.; Rapoport, H. J. Org. Chem. 1979, 44, 4536-4543.
48. Martell, A. E.; Smith, R. M. Critical Stability Constants; Penum Press: New York, 1974.
49. Malhotra, O. P.; Dingh, H. Indian J. Biochem. Biophys. 1976, 13, 316-320
50. Weiser, W.; Lehmann, J.; Matsui, H.; Brewer, C. F.; Hehre, E. J. Arch. Biochem. Biophys. 1992, 292, 493-498.
51. Hanozet, G.; Pircher, H.-P.; Vanni, P.; Oesch, B., Semenza, G. J. Biol. Chem. 1981, 256, 3703-3711.
52. Cleland, W. W. Methods Enzymol. 1979, 63, 103-138.
53. Dixon, M.; Webb, E. C. Enzyme Inhibition and Activation, 3rd ed.; Academic Press: New York, 1979; pp 350-351.