D-Glyconhydroximolactams strongly inhibit α-glycosidases

Carbohydrate Research

Volumn 298, Issue 4, 1997, Pages 291-298

  Hoos, Roland ^a   Vasella, Andrea ^a   Rupitz, Karen ^b   Withers, Stephen G ^b  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

D Gluconhydroximolactam; Glucosidase inhibitors; Jack bean mannosidase; Yeast glucosidase

Indexed keywords

ALPHA GLUCOSIDASE; ALPHA MANNOSIDASE; BETA GLUCOSIDASE; CARBOHYDRATE DERIVATIVE; GLYCOSIDASE; GLYCOSIDASE INHIBITOR; LACTAM DERIVATIVE;

ALCALIGENES FAECALIS; ARTICLE; BEAN; BINDING AFFINITY; DRUG SYNTHESIS; ENZYME BINDING; ENZYME INHIBITION; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT; PRIORITY JOURNAL; PROTON TRANSPORT; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; YEAST;

EID: 0031566318     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(96)00320-5     Document Type: Article

References (41)

1. [1] G.A. Levvy and S.M. Snaith, Adv. Enzymol. Relat. Areas Mol. Biol., 36 (1972) 151-181.
2. [2] M.P. Dale, H.E. Ensley, K. Kern, K.A.R. Sastry, and L.D. Byers, Biochemistry, 24 (1985) 3530-3539.
3. [3] P. Ermert and A. Vasella, Helv. Chim. Acta, 74 (1991) 2043-2053.
4. [4] D.H. Leaback, Biochem. Biophys. Res. Commun., 32 (1968) 1025-1030.
5. [5] M.L. Sinnott, Chem. Rev., 90 (1990) 1171-1202.
6. [6] S.G. Withers, Pure Appl. Chem., 67 (1995) 1673-1682.
7. [7] D. Beer and A. Vasella, Helv. Chim. Acta, 69 (1986) 267-270.
8. [8] H. Ogura, K. Furuhata, H. Takayanagi, N. Tsuzuno, and Y. Iitaka, Bull. Chem. Soc. Jpn., 57 (1984) 2687-2688.
9. [9] M.L. Hackert and R.A. Jacobson, Acta Cryst. B, 27 (1971) 203-209.
10. [10] T.D. Heightman, M. Locatelli, and A. Vasella, Helv. Chim. Acta, 76 (1996) 2190-2200.
11. [11] R.H. Jacobson, X.-J. Zhang, R.F. DuBose, and B.W. Matthews, Nature, 369 (1994) 761-766.
12. [12] T. Barrett, C.G. Suresh, S.P. Tolley, E.J. Dodson, and M.A. Hughes, Structure, 3 (1995) 951-960.
13. [13] S. Jain, W.B. Drendel, Z.W. Chen, F.S. Mathews, W.S. Sly, and J.H. Grubb, Nature Struct. Biol., 3 (1996) 375-381.
14. [14] J. Sakon, W.S. Adney, M.E. Himmel, S.R. Thomas, and P.A. Karplus, Biochemistry, 35 (1996) 10648-10660.
15. [15] M. Qian, R. Haser, G. Buisson, E. Duée, and F. Payan, Biochemistry, 33 (1994) 6284-6294.
16. [16] G. Hanozet, H.-P. Pircher, P. Vanni, B. Oesch, and G. Semenza, J. Biol. Chem., 256 (1981) 3703-3711.
17. [17] P. Ermert, A. Vasella, M. Weber, K. Rupitz, and S.G. Withers, Carbohydr. Res., 250 (1993) 113-128.
18. [18] M.L. Sinnott, Glycosyl group transfer, in M.I. Page and A. Williams (Eds.), Enzyme Mechanisms, The Royal Society of Chemistry, London, 1987, pp. 259-297.
19. [19] Y. Shibata, Y. Kosuge, T. Mizukoshi, and S. Ogawa, Carbohydr. Res., 228 (1992) 377-398.
20. [20] H. Dietrich and R.R. Schmidt, Carbohydr. Res., 250 (1993) 161-176.
21. [21] J.C. Briggs, A.H. Haines, and R.J.K. Taylor, J. Chem. Soc., Chem. Commun., (1993) 1410-1411.
22. [22] P.A. Fowler, A.H. Haines, R.J.K. Taylor, E.J.T. Chrystal, and M.B. Gravestock, J. Chem. Soc. Perkin 1, (1994) 2229-2235.
23. [23] S. Knapp, A. Purandare, K. Rupitz, and S.G. Withers, J. Am. Chem. Soc., 116 (1994) 7461-7462.
24. [24] K. Tatsuta, S. Miura, S. Ohta, and H. Gunji, J. Antibiot., 48 (1995) 286-288.
25. [25] J.D. McCarter and S.G. Withers, J. Am. Chem. Soc., 118 (1996) 241-242.
26. [26] M. Therisod, H. Therisod, and A. Lubineau, Bioorg. Med. Chem. Lett., 5 (1995) 2055-2058.
27. [27] R. Hoos, A.B. Naughton, W. Thiel, A. Vasella, W. Weber, K. Rupitz, and S.G. Withers, Helv. Chim. Acta, 76 (1993) 2666-2686.
28. [28] B. Ganem and G. Papandreou, J. Am. Chem. Soc., 113 (1991) 8984-8985.
29. [29] G. Papandreou, M.K. Tong, and B. Ganem, J. Am. Chem. Soc., 115 (1993) 11682-11690.
30. [30] I.H. Segel, Enzyme Kinetics, Wiley, New York, 1975.
31. [31] P. Ermert, unpublished results.
32. [32] H. Lineweaver and D. Burk, J. Am. Chem. Soc., 56 (1934) 658-666.
33. [33] C. Frieden, J. Biol. Chem., 245 (1970) 5788-5799.
34. [34] G. Legler, Adv. Carbohydr. Chem. Biochem., 48 (1990) 319-384.
35. [35] G. Legler and W. Lotz, Hoppe-Seyler's Z. Physiol. Chem., 354 (1973) 243-254.
36. [36] T. Kajimoto, K.K.-C. Liu, R.L. Pederson, Z. Zhong, Y. Ichikawa, J.A. Porco, and C.-H. Wong, J. Am. Chem. Soc., 113 (1991) 6187-6196.
37. [37] G.W.J. Fleet, S.J. Nicholas, P.W. Smith, S.V. Evans, L.E. Fellows, and R.J. Nash, Tetrahedron Lett., (1985) 3127-3130.
38. [38] M.J. Eis, C.J. Rule, B.A. Wurzburg, and B. Ganem, Tetrahedron Lett., (1985) 5397-5398.
39. [39] I. Vlattas, L. Della Vechia, and J.J. Fitt, J. Org. Chem., 38 (1973) 3749-3752.
40. [40] S.G. Withers, K. Rupitz, D. Trimbur, and R.A.J. Warren, Biochemistry, 31 (1992) 9979-9985.
41. [41] P. Ermert, Dissertation, ETH Zürich, 1996.