Saccharide-peptide hybrids as novel oligosaccharide mimetics

Angewandte Chemie (International Edition in English)

Volumn 34, Issue 23, 1996, Pages 2712-2713

  Wessel, Hans Peter ^a   Mitchell, Catherine M ^a,c,d   Lobato, Cinta Maria ^a,b,c   Schmid, Gérard ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

^b UNIVERSITY OF BARCELONA   (Spain)

^c UNIVERSITY OF BASEL   (Switzerland)

^d UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Carbohydrate amino acids; Compound libraries; Normuramic acid; Oligosaccharide mimetics

Indexed keywords

EID: 33751127305     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (47)

1. a) E. Truscheit, W. Frommer, B. Junge, L. Müller, D. D. Schmidt, W. Wingender, Angew. Chem. 1981, 93, 738; Angew. Chem. Int. Ed. Engl. 1981, 20, 744;
2. a) E. Truscheit, W. Frommer, B. Junge, L. Müller, D. D. Schmidt, W. Wingender, Angew. Chem. 1981, 93, 738; Angew. Chem. Int. Ed. Engl. 1981, 20, 744;
3. b) L. E. Fellows, Chem. Brit. 1987, 23, 847;
4. c) N. M. Carpenter, G. W. Fleet, I. Cenci di Bello, B. Winchester, L. E. Fellows, R. J. Nash, Tetrahedron Lett. 1989, 30, 7261;
5. d) M. L. Sinott, Chem. Rev. 1990, 90, 1171;
6. e) G. Legler, Adv. Carbohydr. Chem. Biochem. 1990, 48, 319;
7. f) H. Paulsen, M. Matzke, B. Orthen, R. Muck, W. Reutter, Liebigs Ann. Chem. 1990, 953;
8. g) G. Papandreou, M. K. Tong, B. Ganem, J. Am. Chem. Soc. 1993, 115, 11682.
9. a) D. Rouzaud, P. Sinaÿ, J. Chem. Soc. Chem. Commun. 1983, 1353;
10. b) B. Giese, T. Witzel, Angew. Chem. 1986, 98, 459; Angew. Chem. Int. Ed. Engl. 1986, 25, 450;
11. b) B. Giese, T. Witzel, Angew. Chem. 1986, 98, 459; Angew. Chem. Int. Ed. Engl. 1986, 25, 450;
12. c) O. R. Martin, F. Xie, R. Kakarla, R. Benhamza, Synlett 1993, 165;
13. d) B. Vauzeilles, D. Cravo, J.-M. Mallet, P. Sinaÿ, ibid. 1993, 522;
14. e) A. Wei, Y. Kishi, J. Org. Chem. 1994, 59, 88;
15. f) L. Lay, F. Nicotra, C. Pangrazio, L. Panza, G. Russo, J. Chem. Soc. Perkin Trans. 1 1994, 333;
16. g) H. Dietrich, R. R. Schmidt, Liebigs Ann. Chem. 1994, 975;
17. h) R. Ferritto, P. Vogel, Tetrahedron Asymm. 1994, 5, 2077.
18. T. Haneda, P. G. Goekjian, S. H. Kim, Y. Kishi, J. Org. Chem. 1992, 57, 490.
19. a) R. J. Ferrier, N. Prasad, J. Chem. Soc. C 1969, 581;
20. b) J. Jurczak, T. Bauer, S. Jarosz, Tetrahedron Lett. 1984, 25, 4809;
21. c) B. Giese, B. Rückert, K. S. Gröninger, R. Mutin, H. J. Lindner, Liebigs Ann. Chem. 1988, 997;
22. d) R. W. Armstrong, B. R. Teegarden, J. Org. Chem. 1992, 57, 915;
23. e) H. P. Wessel, G. Englert, J. Carbohydr. Chem. 1995, 14, 179.
24. a) B. Aebischer, J. H. Bien, R. Prewo, A. Vasella, Helv. Chim. Acta 1982, 65, 2251;
25. b) J. M. Beau, P. Sinaÿ, Tetrahedron Lett. 1985, 26, 6189, 6193;
26. c) S. J. Danishefsky, W. H. Pearson, F. D. Harvey, C. J. Maring, J. P. Springer, J. Am. Chem. Soc. 1985, 107, 1256;
27. d) I. M. Dawson, T. Johnson, R. M. Paton, R. A. C. Rennie, J. Chem. Soc. Chem. Commun. 1988, 1339;
28. e) W. B. Motherwell, B. K. Ross, M. J. Tozer, Synlett 1989, 68;
29. f) A. de Raadt, A. E. Stütz, Carbohydr. Res. 1991, 220, 101;
30. g) R. R. Schmidt, A. Beyerbach, Liebigs Ann. Chem. 1992, 983;
31. h) H. M. Binch, A. M. Griffin, S. Schmidetzki, M. V. J. Ramsey, T. Gallagher, F. W. Lichtenthaler, J. Chem. Soc. Chem. Commun. 1995, 967.
32. a) S. Jarosz, D. Mootoo, B. Fraser-Reid, Carhohydr. Res. 1986, 147, 59;
33. b) S. M. Daly, R. W. Armstrong, Tetrahedron Lett. 1989, 30, 5713;
34. c) J. Alzeer, A. Vasella, Helv. Chim. Acta 1995, 78, 177.
35. Muramic acid (= (R)-2-amino-3-O-(1-carboxyethyl)-2-deoxy-D-glucose) is found in the bacterial cell wall.
36. E. Graf von Roedern, H. Kessler, Angew. Chem. 1994, 106, 684; Angew. Chem. Int. Ed. Engl. 1994, 33, 687.
37. E. Graf von Roedern, H. Kessler, Angew. Chem. 1994, 106, 684; Angew. Chem. Int. Ed. Engl. 1994, 33, 687.
38. A similar approach has been mentioned in the context of nucleoside mimetics synthesis: K. C. Nicolaou, H. Flörke, M. G. Egan, T. Barth, V. A. Estevez, Tetrahedron Lett. 1995, 36, 1775.
39. a) R. Gigg, P. M. Carroll, Nature 1961, 191, 495;
40. b) T. Miyazaki, Y. Matsushima, Bull. Chem. Soc. Jpn. 1968, 41, 2723.
41. Dissociation constants of carbohydrate-protein complexes are generally in the upper micromolar range, as hydrogen bonding dominates, and strong hydrophobic interactions are missing; cf. C.-H. Wong, R. L. Halcomb, Y. Ichikawa, T. Kajimoto, Angew. Chem. 1995, 1067, 569; Angew. Chem. Int. Ed. Engl. 1995, 34, 521.
42. Dissociation constants of carbohydrate-protein complexes are generally in the upper micromolar range, as hydrogen bonding dominates, and strong hydrophobic interactions are missing; cf. C.-H. Wong, R. L. Halcomb, Y. Ichikawa, T. Kajimoto, Angew. Chem. 1995, 1067, 569; Angew. Chem. Int. Ed. Engl. 1995, 34, 521.
43. P. C. Wyss, J. Kiss, Helv. Chim. Acta 1979, 58, 1833.
44. W. Meyer zu Reckendorf, B. Radatus, E. Bischof, R. Weber, Chem. Ber. 1974, 107, 869. We have prepared 7 from the N-Z-protected precursor (H. P. Wessel, J. Carbohydr. Chem. 1988, 7, 263).
45. W. Meyer zu Reckendorf, B. Radatus, E. Bischof, R. Weber, Chem. Ber. 1974, 107, 869. We have prepared 7 from the N-Z-protected precursor (H. P. Wessel, J. Carbohydr. Chem. 1988, 7, 263).
46. Z. J. Kaminski, Synthesis 1987, 419.
47. 6]DMSO, TMS): δ = 8.20 (d, 1H, J = 8.7 Hz, NH), 8.15 (d, 1H, J = 8.6 Hz, NH), 7.94 (d, 1H, J = 8.6 Hz, NH), 7.76 (br. d, 1H, J≈7.2 Hz, NH).