Parallel synthesis of sialyl Lewis X mimetics on a solid phase: Access to a library of fucopeptides

Angewandte Chemie - International Edition

Volumn 37, Issue 12, 1998, Pages 1707-1711

  Lampe, Thomas F J ^a   Weitz Schmidt, Gabriele ^b   Wong, Chi Huey ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b NOVARTIS PHARMA AG   (Switzerland)

Author keywords

Glycopeptides; Parallel synthesis; Sialyl Lewis X mimetics; Solid phase synthesis

Indexed keywords

EID: 0032479252     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980703)37:12<1707::AID-ANIE1707>3.0.CO;2-V     Document Type: Article

References (49)

1. a) T. A. Springer, Cell 1994, 76, 301, and references therein;
2. b) J. C. Paulson in Adhesion: Its Role in Inflammatory Disease (Ed.: L. Harlow, D. Liu), Freemann, New York, 1992.
3. a) M. Buerke, A. S. Weyrich, Z. Zheng, F. C. A. Gaeta, M. J. Forrest, A. M. Lefer, J. Clin. Invest. 1994, 1140;
4. b) A. Giannis, Angew. Chem. 1994, 106, 188; Angew. Chem. Int. Ed. Engl. 1994, 33, 178.
5. b) A. Giannis, Angew. Chem. 1994, 106, 188; Angew. Chem. Int. Ed. Engl. 1994, 33, 178.
6. x mimetics, see E. E. Simanek, G. J. McGarvey, J. A. Jablonowski, C.-H. Wong, Chem. Rev., in press and references therein.
7. B. J. Graves, R. L. Crowther, C. Chandran, J. M. Rumberger, S. Li, K.-S. Huang, D. H. Presky, P. C. Familletti, B. A. Wolitzky, D. K. Burnes, Nature 1994, 367, 532.
8. For solution conformations, see a) Y. Ichikawa, Y. C. Lin, D. P. Dumas, G. J. Shen, E. Garcia-Junceda, M. A. Williams, R. Bayer, C. Ketcham, L. E. Walker, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc. 1992, 114, 9283; for conformations bound to E-selectin, see b) R. M. Cooke, R. S. Hale, S. G. Lister, G. Shah, M. P. Weir, Biochemistry 1994, 33, 10591; c) L. Scheffler, B. Ernst, A. Katopodis, J. L. Magnani, W. J. Wang, R. Weisema, T. Peters, Angew. Chem. 1995, 107, 2034; Angew. Chem. Int. Ed. Engl. 1995, 34, 1841; for conformations bound to E-, P-, and L-selectins, see d) L. Poppe, G. S. Brown, J. S. Philo, P. V. Nikrad, B. H. Shah, J. Am. Chem. Soc. 1997, 119, 1727.
9. For solution conformations, see a) Y. Ichikawa, Y. C. Lin, D. P. Dumas, G. J. Shen, E. Garcia-Junceda, M. A. Williams, R. Bayer, C. Ketcham, L. E. Walker, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc. 1992, 114, 9283; for conformations bound to E-selectin, see b) R. M. Cooke, R. S. Hale, S. G. Lister, G. Shah, M. P. Weir, Biochemistry 1994, 33, 10591; c) L. Scheffler, B. Ernst, A. Katopodis, J. L. Magnani, W. J. Wang, R. Weisema, T. Peters, Angew. Chem. 1995, 107, 2034; Angew. Chem. Int. Ed. Engl. 1995, 34, 1841; for conformations bound to E-, P-, and L-selectins, see d) L. Poppe, G. S. Brown, J. S. Philo, P. V. Nikrad, B. H. Shah, J. Am. Chem. Soc. 1997, 119, 1727.
10. For solution conformations, see a) Y. Ichikawa, Y. C. Lin, D. P. Dumas, G. J. Shen, E. Garcia-Junceda, M. A. Williams, R. Bayer, C. Ketcham, L. E. Walker, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc. 1992, 114, 9283; for conformations bound to E-selectin, see b) R. M. Cooke, R. S. Hale, S. G. Lister, G. Shah, M. P. Weir, Biochemistry 1994, 33, 10591; c) L. Scheffler, B. Ernst, A. Katopodis, J. L. Magnani, W. J. Wang, R. Weisema, T. Peters, Angew. Chem. 1995, 107, 2034; Angew. Chem. Int. Ed. Engl. 1995, 34, 1841; for conformations bound to E-, P-, and L-selectins, see d) L. Poppe, G. S. Brown, J. S. Philo, P. V. Nikrad, B. H. Shah, J. Am. Chem. Soc. 1997, 119, 1727.
11. For solution conformations, see a) Y. Ichikawa, Y. C. Lin, D. P. Dumas, G. J. Shen, E. Garcia-Junceda, M. A. Williams, R. Bayer, C. Ketcham, L. E. Walker, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc. 1992, 114, 9283; for conformations bound to E-selectin, see b) R. M. Cooke, R. S. Hale, S. G. Lister, G. Shah, M. P. Weir, Biochemistry 1994, 33, 10591; c) L. Scheffler, B. Ernst, A. Katopodis, J. L. Magnani, W. J. Wang, R. Weisema, T. Peters, Angew. Chem. 1995, 107, 2034; Angew. Chem. Int. Ed. Engl. 1995, 34, 1841; for conformations bound to E-, P-, and L-selectins, see d) L. Poppe, G. S. Brown, J. S. Philo, P. V. Nikrad, B. H. Shah, J. Am. Chem. Soc. 1997, 119, 1727.
12. For solution conformations, see a) Y. Ichikawa, Y. C. Lin, D. P. Dumas, G. J. Shen, E. Garcia-Junceda, M. A. Williams, R. Bayer, C. Ketcham, L. E. Walker, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc. 1992, 114, 9283; for conformations bound to E-selectin, see b) R. M. Cooke, R. S. Hale, S. G. Lister, G. Shah, M. P. Weir, Biochemistry 1994, 33, 10591; c) L. Scheffler, B. Ernst, A. Katopodis, J. L. Magnani, W. J. Wang, R. Weisema, T. Peters, Angew. Chem. 1995, 107, 2034; Angew. Chem. Int. Ed. Engl. 1995, 34, 1841; for conformations bound to E-, P-, and L-selectins, see d) L. Poppe, G. S. Brown, J. S. Philo, P. V. Nikrad, B. H. Shah, J. Am. Chem. Soc. 1997, 119, 1727.
13. a) B. K. Bradley, M. Kiso, S. Abbas, P. Nikrad, O. Strivastava, C. Foxall, Y. Oda, A. Hasegawa, Glycobiology, 1993, 3, 633;
14. b) W. Stahl, U. Sprengard, G. Kretzschmar, H. Kunz, Angew. Chem. 1994, 106, 2186; Angew. Chem. Int. Ed. Engl. 1994, 33, 2096;
15. b) W. Stahl, U. Sprengard, G. Kretzschmar, H. Kunz, Angew. Chem. 1994, 106, 2186; Angew. Chem. Int. Ed. Engl. 1994, 33, 2096;
16. c) S. A. DeFrees, F. C. A. Gaeta, Y. C. Lin, Y. Ichikawa, C.-H. Wong, J. Am. Chem. Soc. 1993, 115, 7549.
17. a) S.-H. Wu, M. Shimazaki, C.-C. Lin, L. Qiao, W. J. Moree, G. Weitz-Schmidt, C.-H. Wong, Angew. Chem. 1996, 108, 106; Angew. Chem. Int. Ed. Engl. 1996, 35, 88;
18. a) S.-H. Wu, M. Shimazaki, C.-C. Lin, L. Qiao, W. J. Moree, G. Weitz-Schmidt, C.-H. Wong, Angew. Chem. 1996, 108, 106; Angew. Chem. Int. Ed. Engl. 1996, 35, 88;
19. b) C.-H. Wong, F. Moris-Varas, S.-C. Hung, T. G. Maron, C.-C. Lin, K. W. Gong, G. Weitz-Schmidt, J. Am. Chem. Soc. 1997, 119, 8152;
20. c) H. C. Kolb, B. Ernst, Chem. Eur. J. 1997, 3, 1571;
21. d) For early work on glycopeptides as mannose 6-phosphate mimics, see M. K. Christensen, M. Meldal, K. Bock, H. Cordes, S. Mouristen, H. Elsner, J. Chem. Soc. Perkin Trans. 1 1994, 1299.
22. a) M. A. Gallop, R. W. Barrett, W. P. Dower, S. P. A. Fodor, E. M. Gordo, J. Med. Chem. 1994, 37, 1233;
23. b) E. M. Gordon, R. W. Barrett, W. J. Dower, S. P. A. Fodor, M. A. Gallop, ibid. 1994, 37, 1385;
24. c) J. S. Früchtel, G. Jung, Angew. Chem 1996, 108, 19; Angew. Chem. Int. Ed. Engl. 1996, 35, 17;
25. c) J. S. Früchtel, G. Jung, Angew. Chem 1996, 108, 19; Angew. Chem. Int. Ed. Engl. 1996, 35, 17;
26. d) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, ibid. 1996, 108, 2436; 1996, 35, 2288;
27. d) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, ibid. 1996, 108, 2436; 1996, 35, 2288;
28. e) Combinatorial Peptide and Nonpeptide Libraries (Ed.; G. Jung), VCH, Weinheim, 1996;
29. f) K. S. Lam, M. L. V. Krchnak, Chem. Rev. 1997, 97, 411;
30. g) A. Nefzi, J. M. Ostresh, R. A. Houghten, ibid. 1997, 97, 449.
31. Anchoring of 1,3-and 1,2-diols on solid supports: a) J. M. J. Frechet, G. Pelle, J. Chem. Soc. Chem. Commun. 1975, 225; b) E. Seymour, J. M. J. Frechet, Tetrahedron Lett. 1976, 3669; c) S. Hanessian, T. Ogawa, Y. Guindon, J. L. Kamennof, R. Roy, Carbohydr. Res. 1974, 38, C15; d) Y. Palom, E. Alazzouzi, F. Gordillo, A. Grandas, E. Pedroso, Tetrahedron Lett. 1993, 34, 2195; e) G. T. Wang, S. Li, N. Wideburg, G. A. Krafft, D. J. Kempf, J. Med. Chem. 1995, 38, 2995.
32. Anchoring of 1,3-and 1,2-diols on solid supports: a) J. M. J. Frechet, G. Pelle, J. Chem. Soc. Chem. Commun. 1975, 225; b) E. Seymour, J. M. J. Frechet, Tetrahedron Lett. 1976, 3669; c) S. Hanessian, T. Ogawa, Y. Guindon, J. L. Kamennof, R. Roy, Carbohydr. Res. 1974, 38, C15; d) Y. Palom, E. Alazzouzi, F. Gordillo, A. Grandas, E. Pedroso, Tetrahedron Lett. 1993, 34, 2195; e) G. T. Wang, S. Li, N. Wideburg, G. A. Krafft, D. J. Kempf, J. Med. Chem. 1995, 38, 2995.
33. Anchoring of 1,3-and 1,2-diols on solid supports: a) J. M. J. Frechet, G. Pelle, J. Chem. Soc. Chem. Commun. 1975, 225; b) E. Seymour, J. M. J. Frechet, Tetrahedron Lett. 1976, 3669; c) S. Hanessian, T. Ogawa, Y. Guindon, J. L. Kamennof, R. Roy, Carbohydr. Res. 1974, 38, C15; d) Y. Palom, E. Alazzouzi, F. Gordillo, A. Grandas, E. Pedroso, Tetrahedron Lett. 1993, 34, 2195; e) G. T. Wang, S. Li, N. Wideburg, G. A. Krafft, D. J. Kempf, J. Med. Chem. 1995, 38, 2995.
34. Anchoring of 1,3-and 1,2-diols on solid supports: a) J. M. J. Frechet, G. Pelle, J. Chem. Soc. Chem. Commun. 1975, 225; b) E. Seymour, J. M. J. Frechet, Tetrahedron Lett. 1976, 3669; c) S. Hanessian, T. Ogawa, Y. Guindon, J. L. Kamennof, R. Roy, Carbohydr. Res. 1974, 38, C15; d) Y. Palom, E. Alazzouzi, F. Gordillo, A. Grandas, E. Pedroso, Tetrahedron Lett. 1993, 34, 2195; e) G. T. Wang, S. Li, N. Wideburg, G. A. Krafft, D. J. Kempf, J. Med. Chem. 1995, 38, 2995.
35. Anchoring of 1,3-and 1,2-diols on solid supports: a) J. M. J. Frechet, G. Pelle, J. Chem. Soc. Chem. Commun. 1975, 225; b) E. Seymour, J. M. J. Frechet, Tetrahedron Lett. 1976, 3669; c) S. Hanessian, T. Ogawa, Y. Guindon, J. L. Kamennof, R. Roy, Carbohydr. Res. 1974, 38, C15; d) Y. Palom, E. Alazzouzi, F. Gordillo, A. Grandas, E. Pedroso, Tetrahedron Lett. 1993, 34, 2195; e) G. T. Wang, S. Li, N. Wideburg, G. A. Krafft, D. J. Kempf, J. Med. Chem. 1995, 38, 2995.
36. Although C-terminal modified peptide amides and esters are accessible by using specific linker groups, the approaches reported so far are not adaptable to combinatorial methodologies. More synthetic flexibility has been introduced by the concept of postsynthetic C-N inversion on the solid phase: a) M. Davies, M. Bradley, Angew. Chem. 1997, 109, 1135; Angew. Chem. Int. Ed. Engl. 1997, 36, 1097; b) R. S. Kania, R. N. Zuckermann, C. K. Marlowe, J. Am Chem. Soc. 1994, 116, 8835.
37. Although C-terminal modified peptide amides and esters are accessible by using specific linker groups, the approaches reported so far are not adaptable to combinatorial methodologies. More synthetic flexibility has been introduced by the concept of postsynthetic C-N inversion on the solid phase: a) M. Davies, M. Bradley, Angew. Chem. 1997, 109, 1135; Angew. Chem. Int. Ed. Engl. 1997, 36, 1097; b) R. S. Kania, R. N. Zuckermann, C. K. Marlowe, J. Am Chem. Soc. 1994, 116, 8835.
38. Although C-terminal modified peptide amides and esters are accessible by using specific linker groups, the approaches reported so far are not adaptable to combinatorial methodologies. More synthetic flexibility has been introduced by the concept of postsynthetic C-N inversion on the solid phase: a) M. Davies, M. Bradley, Angew. Chem. 1997, 109, 1135; Angew. Chem. Int. Ed. Engl. 1997, 36, 1097; b) R. S. Kania, R. N. Zuckermann, C. K. Marlowe, J. Am Chem. Soc. 1994, 116, 8835.
39. a) J. Y. Ramphal, M. Hiroshige, B. Lou, J. J. Gaudino, M. Hayashi, S. M. Chen, L. C. Chiang, F. C. A. Gaeta, S. A. DeFrees, J. Med. Chem. 1996, 39, 1357;
40. b) H. Tsujishita, Y. Hiramatsu, N. Kondon, H. Ohmoto, H. Kondo, M. Kiso, A. Hasegawa, ibid. 1997, 40, 362.
41. S. Sato, M. Mori, Y. Ito, T. Ogawa, Carbohydr. Res. 1986, 155, C6.
42. E. Bayer, Angew. Chem. 1991, 103, 117; Angew. Chem. Int. Ed. Engl. 1991, 30, 113.
43. E. Bayer, Angew. Chem. 1991, 103, 117; Angew. Chem. Int. Ed. Engl. 1991, 30, 113.
44. H. Kunz, H. Waldmann, Angew. Chem. 1984, 86, 49; Angew. Chem. Int. Ed. Engl. 1984, 23, 71.
45. H. Kunz, H. Waldmann, Angew. Chem. 1984, 86, 49; Angew. Chem. Int. Ed. Engl. 1984, 23, 71.
46. P. Sieber, Tetrahedron. Lett. 1987, 28, 6147.
47. a polylysine conjugate assay:
48. b) G. Thoma, J. L. Magnani, R. Ohrlein, B. Ernst, F. Schwarzenbach, R. Duthaler, J. Am. Chem. Soc. 1997, 119, 7414.
49. [7a]