The activation of fibroblast growth factors by heparin: Synthesis and structural study of rationally modified heparin-like oligosaccharides

Canadian Journal of Chemistry

Volumn 80, Issue 8, 2002, Pages 917-936

  Ojeda, Rafael ^a   Angulo, Jesús ^a   Nieto, Pedro M ^a   Martín Lomas, Manuel ^a  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

Author keywords

Conformational analysis; FGF activation; Heparin oligosaccharides; Synthesis design

Indexed keywords

CONFORMATIONS; DIMERIZATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOMERS; SYNTHESIS (CHEMICAL);

HELICAL STRUCTURES;

POLYSACCHARIDES;

CARBOHYDRATE DERIVATIVE; FIBROBLAST GROWTH FACTOR; HEPARIN DERIVATIVE; OLIGOSACCHARIDE;

ARTICLE; CONFORMATION; DIMERIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

EID: 0036434884     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v02-023     Document Type: Article

References (62)

1. P. Klint and L. Claesson-Welsh. Front. Biosci. 4, 165, (1999).
2. H.E. Conrad. Heparin-binding Proteins. Academic Press, San Diego. 1998.
3. S. Faham, R.J. Linhardt, and D.C. Rees. Curr. Opin. Struct. Biol. 8, 578, (1998).
4. M. Klagsbrun. Semin. Cancer Biol. 3, 81, (1993).
5. D.M. Ornitz, A.B. Herr, M. Nilsson, J. Westman, C.M. Svahn, and K. Waksman. Science (Washington, D.C.), 268, 432 (1995).
6. S. Faham, R.E. Hileman, J. Fromm, R. Linhardt, and D.C. Rees. Science (Washington, D.C.), 271, 116 (1996).
7. A.D. DiGabriele, I. Lax, D.I. Chen, C.M. Svahn, M. Jaye, J. Schlessinger, and W.A. Hendrickson. Nature (London), 393, 812 (1998).
8. A.N. Plotnikov, J. Schlessinger, S.R. Hubbard, and M. Mohammadi. Cell (Cambridge, Mass.), 98, 641 (1999).
9. D.J. Stauber, A.D. DiGabriele, and W.A. Hendrickson. Proc. Natl. Acad. Sci. U.S.A. 97, 49 (2000).
10. J. Schlessinger, A.N. Plotnikov, O.A. Ibrahimi, A. Eliseenkova, B.K. Yeh, A. Yayon, R.J. Linhardt, and M. Mohammadi. Mol. Cell 6, 743 (2000).
11. L. Pellegrini, D.F. Burke, F. Von Dolft, B. Mulloy, and T.I. Blundell. Nature (London), 407, 1029 (2000).
12. F.Y. Zhou, M. Kan, R.T. Owens, W.L. McKeehan, J.A. Thompson, R.J. Linhardt, and M. Höök. Eur. J. Cell. Biol. 73, 71 (1997).
13. T. Spivak-Kroizman, M.A. Lemmon, I. Dikic, J.E. Ladbury, D. Pinchasi, J. Huang, M. Jaye, G. Crumley, J. Schlessinger, and I. Lax. Cell (Cambridge, Mass.), 79, 1015 (1994).
14. A.B. Herr, D.M. Ornitz, R. Sasisekharan, G. Venkataraman, and G. Waksman. J. Biol. Chem. 272, 16 382 (1997).
15. F.J. Moy, M. Safran, A.P. Seddon, D. Kitchen, P. Bohlen, D. Aviezer, A. Yayon, and R. Powers. Biochemistry, 36, 4782 (1997).
16. G. Waksman and A.B. Herr. Nat. Struct. Biol. 5, 527 (1998).
17. G. Venkataraman, R. Raman, V. Sasisekharan, and R. Sasisekharan. Proc. Natl. Acad. Sci. U.S.A. 96, 3658 (1999).
18. B. Casu. Adv. Carbohydr. Chem. Biochem. 43, 51 (1985).
19. S.E. Stringer and J.T. Gallagher. Int. J. Biochem. Cell. Biol. 29, 709 (1997).
20. M. Salmivirta, M.K. Lidholt, and U. Lindahl. FASEB J. 10, 1270 (1996).
21. J.L. de Paz, J. Angulo, J.M. Lassaletta, P.M. Nieto, M. Redondo-Horcajo, R.M. Lozano, G. Giménez-Gallego, and M. Martín-Lomas. ChemBioChem. 2, 101 (2001).
22. J. Kovensky, P. Duchaussoy, M. Petitou, and P. Sinaÿ. Tetrahedron: Asymmetry, 7, 3119 (1996).
23. J. Kovensky, P. Duchaussoy, F. Bono, M. Salmivirta, P. Sizun, J.M. Herbert, M. Petitou, and P. Sinaÿ. Bioorg. Med. Chem. 7, 1567 (1999).
24. C. Tabeur, J.M. Mallet, F. Bono, J.M. Herbert, M. Petitou, and P. Sinaÿ. Biorg. Med. Chem. 7, 2003 (1999).
25. (a) B. La Ferla, L. Lay, M. Guerini, L. Poletti, L. Panza, and G. Russo. Tetrahedron, 55, 9867 (1999);
26. (b) L. Poletti, M. Fleischer, C. Vogel, M. Guerrini, G. Torri, and L. Lay. Eur. J. Org. Chem. 2727 (2001).
27. B. Mulloy, M.J. Foster, C. Jones, and D.B. Davis. Biochem. J. 293, 849 (1993).
28. D. Mikhailov, K.H. Mayo, I.R. Vlahov, T. Toida, A. Pervin, and R.L. Linhardt. Biochem. J. 318, 93 (1996).
29. D. Mikhailov, R.L. Linhardt, and K.H. Mayo. Biochem. J. 328, 51 (1997).
30. G. Torri, B. Casu, G. Gatti, M. Petitou, J. Choay, J.-C. Jacquinet, and P. Sinaÿ. Biochem. Biophys. Res. Commun. 128, 138 (1985).
31. B. Casu, J. Choay, D.R. Ferro, G. Gatti, J.-C. Jacquinet, M. Petitou, A. Provasoli, M. Ragazzi, P. Sinaÿ, and G. Torri. Nature (London), 322, 215 (1986).
32. A. Walker, J.E. Turnbull, and J.T. Gallagher. J. Biol. Chem. 269, 931 (1994).
33. D.M. Ornitz, A. Yayon, J.G. Flanagan, C.M. Svahn, E. Levi, and P. Leder. Mol. Cell. Biol. 12, 240 (1992).
34. H. Wang, T. Toida, Y.S. Kim, I. Capila, R.Y. Hileman, M. Bernfield, and R.J. Linhardt. Biochem. Biophys. Res. Commun. 235, 369 (1997).
35. M. Ishihara, D.J. Tyrell, G.B. Stauber, S. Brown, L.S. Cousens, and R.J. Stack. J. Biol. Chem. 268, 4675 (1993).
36. D. Avizer, E. Levy, M. Safran, C. Svahn, E. Buddecke, A. Schmidt, G. David, I. Vlodavsky, and A. Yayon. J. Biol. Chem. 269, 114 (1994).
37. P.J. Garegg, H. Hultberg, and S. Wallin. Carbohydr. Res. 108, 97 (1982).
38. T. Rosen, I.M. Lico, and D.T.W. Chu. J. Org. Chem. 53, 1580 (1988).
39. L. Van Hijte and R.D. Little. J. Org. Chem. 50, 3940 (1985).
40. K.C. Nicolaou, C.A. Veale, C. K. Hwang, J. Hutchinson, C.V.C. Prasad, and W.W. Ogilvie. Angew. Chem. Int. Ed. Engl. 30, 299 (1991).
41. S.A. Abbas and A.H. Haines. Carbohydr. Res. 39, 358 (1975).
42. L. Rochepeau-Jobron and J.C. Jacquinet. Carbohydr. Res. 305, 181 (1988).
43. H. Lucas, J.E.M. Basten, T.G. Van Dinther, D.G. Mauleman, S.F. Van Aelst, and C.A.A. van Boeckel. Tetrahedron, 46, 8207 (1990).
44. R. Ojeda, J.L. de Paz, M. Martín-Lomas, and J.M. Lassaletta. Synlett. 8, 1316 (1999).
45. D. Tailler, J.C. Jacquinet, A.M. Noirot, and J.M. Beau. J. Chem. Soc. Perkin Trans. 1, 3163 (1992).
46. E.A. Yates, F. Santini, B. De Cristofano, N. Payre, C. Cosentino, M. Guerrini, A. Naggi, G. Torri, and M. Hricovini. Carbohydr. Res. 329, 239 (2000).
47. B. Mulloy, M.J. Forster, C. Jones, A.F. Drake, E.A. Johnson, and D.B. Davies. Carbohydr. Res. 255, 1 (1994).
48. D. Jeannerat and G. Bodenhausen. J. Magn. Reson. 141, 133 (1999).
49. D. Ferro, A. Provasoli, M. Ragazzi, B. Casu, G. Torri, V. Bossennec, B. Perly, P. Sinaÿ, M. Petitou, and J. Choay. Carbohydr. Res. 195, 157 (1990);
50. C.A.A. van Boeckel, S.F. van Aelst, G.N. Wagenaars, J.-R. Mellema, H. Paulsen, T. Peters, A. Pollex, and V. Sinnwell. Recl. Trav. Chim. Pays-Bas, 106, 19 (1987).
51. D.A. Cumming and J.P. Carver. Biochemistry, 26, 6664 (1995).
52. M. Hricovini and G. Torri. Carbohydr. Res. 268, 159 (1995).
53. A.L. Davis, E.D. Laue, J. Keeler, D. Moskau, and J. Lohman. J. Magn. Reson. 94, 637 (1991).
54. A. Bax and D.G. Davis. J. Magn. Reson. 65, 355 (1985).
55. J. Schleucher, M. Schwendinger, M. Sattler, P. Schmidt, O. Schedletzky, S.J. Glaser, O.W. Sorensen, and C. Griesinger. J. Biomol. NMR, 4, 301 (1994).
56. G. Bodenhausen, R.L. Vold, and R.R. Vold. J. Magn. Reson. 37, 93 (1980).
57. R. Wagner and S. Berger. J. Magn. Reson. Ser. A, 123, 119 (1996).
58. D. Neuhaus and M. Williamson. The Nuclear Overhauser Effect in Structural and Conformational Analysis. VCH, New York. 1989.
59. S.J. Weiner, P.A. Kollman, D.T. Nguyen, and D.A. Case. J. Comp. Chem. 7, 230 (1986).
60. D.A. Case, D.A. Pearlman, J.W. Caldwell, T.E. Cheatham, III, W.S. Ross, C.L. Simmerling, T.A. Darden, K.M. Merz, R.V. Stanton, A.L. Cheng, J.J. Vincent, M. Crowley, D.M. Ferguson, R.J. Radmer, G.L. Seibel, U.C. Singh, P.K. Weiner, and P.A. Kollman. AMBER 5. University of California, San Francisco. 1997.
61. R.J. Woods, R.A. Dwek, C.J. Edge, and B. Fraser-Reid. J. Phys. Chem. 99, 3832 (1995).
62. C.J.M. Huige and C. Altona. Comp. Chem. 16, 56 (1995).