Glycopeptides as oligosaccharide mimics: High affinity sialopeptide ligands for sialoadhesin from combinatorial libraries

Journal of Combinatorial Chemistry

Volumn 5, Issue 1, 2003, Pages 18-27

  Halkes, Koen M ^a   St Hilaire, Phaedria M ^b   Crocker, Paul R ^c   Meldal, Morten ^a  

^a CARLSBERG LABORATORY   (Denmark)

^b Carlsberg Biosector   (Denmark)

^c UNIVERSITY OF DUNDEE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOPEPTIDE; HEPTAPEPTIDE; IMMUNOGLOBULIN; OLIGOSACCHARIDE; PENTAPEPTIDE; RECOMBINANT PROTEIN; SIALIC ACID; SIALOADHESIN; THREONINE; ERYTHROCYTE RECEPTOR; IMMUNOGLOBULIN RECEPTOR; LIGAND; MEMBRANE PROTEIN; SIALOGLYCOPROTEIN;

AMINO TERMINAL SEQUENCE; ARTICLE; BINDING AFFINITY; COMBINATORIAL LIBRARY; LIGAND BINDING; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PEPTIDE SYNTHESIS; PROTEIN DOMAIN; PROTEIN MOTIF; PROTEIN STRUCTURE; SEQUENCE ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SURFACE PLASMON RESONANCE; BINDING COMPETITION; COMBINATORIAL CHEMISTRY; DRUG SCREENING; METABOLISM; METHODOLOGY; MOLECULAR MIMICRY; PHYSIOLOGY; SYNTHESIS;

BINDING, COMPETITIVE; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG EVALUATION, PRECLINICAL; GLYCOPEPTIDES; LIGANDS; MEMBRANE GLYCOPROTEINS; MOLECULAR MIMICRY; OLIGOSACCHARIDES; RECEPTORS, IMMUNOLOGIC; SIALOGLYCOPROTEINS; SURFACE PLASMON RESONANCE;

EID: 0037526362     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0200641     Document Type: Article

References (43)

1. Varki, A. FASEB J. 1997, 11, 248-255.
2. Lasky, L. A. Annu. Rev. Biochem. 1995, 64, 707-713.
3. Schauer, R. Glycoconjugate J. 2000, 17, 485-499.
4. Crocker, P. R.; Gordon, S. J. Exp. Med. 1986, 164, 1862-1875.
5. Stamenkovic, I.; Seed, B. Nature 1990, 345, 74-77.
6. Crocker, P. R.; Varki, A. Trends Immunol. 2001, 22, 337-342.
7. Crocker, P. R.; Clark, E. A.; Filbin, M.; Gordon, S.; Jones, Y.; Kehrl, J. H.; Kelm, S.; Le Douarin, N.; Powell, L.; Roder, J.; Schnaar, R. L.; Sgroi, D. C.; Stamenkovic, K.; Schauer, R.; Schachner, M.; van der Merwe, P. A.; Watt, S. M.; Varki, A. Glycobiology 1998, 8, Glycoforum 2 v-vi.
8. Freeman, S. D.; Kelm, S.; Barber, E. K.; Crocker, P. R. Blood 1995, 85, 2005-2012.
9. Kelm, S.; Pelz, A.; Schauer, R.; Filbin, M.; Tang, S.; de Bellard, M.-E. ; Schnaar, R. L.; Mahoney, J. A.; Hatrnell, A.; Bradfield, P.; Crocker, P. R. Sialoadhesin, Curr. Biol. 1994, 4, 965-972.
10. Crocker, P. R.; Mucklow, S.; Bouckson, V.; McWilliam, A. S.; Willis, A. C.; Gordon, S.; Nilon, G.; Kelm, S.; Bradfield, P. Sialoadhesin, A. EMBO J. 1994, 13, 4490-4503.
11. Nath, D.; van der Merwe, P. A.; Kelm, S.; Bradfield, P.; Crocker, P. R. J. Biol. Chem. 1995, 270, 26184-26191.
12. Vinson, M.; van der Merwe, P. A.; Kelm, S.; May, A.; Jones, E. Y.; Crocker, P. R. J. Biol. Chem. 1996, 271, 9267-9272.
13. May, A. P.; Robinson, R. C.; Vinson, M.; Crocker, P. R.; Jones, E. Y. ' Mol. Cell 1998, 1, 719-728.
14. Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1999, 38, 2300-2324.
15. Schweizer, F.; Hindsgaul, O. Curr. Opin. Chem. Biol. 1999, 3, 291-298.
16. Wong, C.-H. Acc. Chem. Res. 1999, 32, 376-385.
17. Meldal, M.; Christiansen-Brams, I.; Christensen, M.; Mouritsen, S.; Bock, K. In Complex Carbohydrates in Drug Research; Bock, K., Clausen, H., Eds.; Munksgaard: Copenhagen, 1994; pp 153-164.
18. Christensen, M.; Meldal, M.; Bock, K.; Cordes, H.; Mouritsen, S.; Elsner, H. ' J. Chem. Soc., Perkin Trans. 1 1994, 1299-1310.
19. Wu, S.-H.; Shimazaki, M.; Lin, C.-C.; Qiao, L.; Moree, W. J.; Weitz-Schmidt, G.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1996, 35, 88-90.
20. Dolle, R. E. J. Comb. Chem. 2001, 3, 477-517.
21. Furka, A.; Sebestyen, F.; Dibo, G. Abstr. 10th Int. Symp. Med. Chem. Budapest 1988, 9, 288.
22. Furka, A.; Sebestyen, F.; Asgedom, M.; Dibo, G. Int. J. Peptide Protein Res. 1991, 37, 487-493.
23. Lam, K. S.; Salmon, S. E.; Hersh, E. M.; Hruby, V. J.; Kazmierski, W. M. ; Knapp, R. J. Nature (London) 1991, 354, 82-84.
24. St. Hilaire, P. M.; Lowary, T.; Bock, K.; Meldal, M. In Peptides 1996: Proceedings of the 24th European Peptide Symposium; Ramage, R., Epton, R., Eds. ; Mayflower Scientific Ltd.: Kingswinford, 1998; pp 817-818.
25. St. Hilaire, P. M.; Lowary, T. L.; Meldal, M.; Bock, K. J. Am. Chem. Soc. 1998, 120, 13312-13320.
26. Youngquist, S. R.; Fuentes, G.; Lacey, M.; Keough, T. J. Am. Chem. Soc. 1995, 117, 3900-3906.
27. Halkes, K.; St. Hilaire, P. M.; Jansson, A. M.; Gotfredsen, C. H.; Meldal, M. J. Chem. Soc., Perkin Trans. 1 2000, 2127-2133.
28. May, A. P.; Robinson, R. C.; Aplin, R. T.; Bradfield, P.; Crocker, P. R. ; Jones, E. Y. Protein Sci. 1997, 6, 717-721.
29. Holmes, C.; Jones, D. J. Org. Chem. 1995, 60, 2318-2319.
30. Valero, M.-L.; Giralt, E.; Andreu, D. Lett. Pept. Sci. 1999, 6, 109-115.
31. Meldal, M.; Juliano, M. A.; Jansson, A. M. Tetrahedron Lett. 1997, 38, 2531-2534.
32. Crocker, P. R.; Vinson, M.; Kelm, S.; Drickamer, K. Biochem. J. 1999, 341, 355-361.
33. Quiocho, F.-A. Acc. Chem. Res. 1989, 61, 1293-1306.
34. Kalinin, N. L.; Ward, L. D.; Winzor, D. J. Anal. Biochem. 1995, 228, 238-244.
35. Haseley, S. R.; Talaga, P.; Kamerling, J. P.; Vliegenthart, J. F. Anal. Biochem. 1999, 274, 203-210.
36. Imberty, A.; Gautier, C.; Lescar, J.; Pérez, S.; Wyns, L.; Loris, R. J. Biol. Chem. 2000, 275, 17541-17548.
37. Mann, D. A.; Kanai, M.; Maly, D. J.; Kiessling, L. L. J. Am. Chem. Soc. 1998, 120, 10575-10582.
38. Prytulla, S.; Lambert, J.; Lauterwein, J.; Klessinger, M.; Thiem, J. Magn. Reson. Chem. 1990, 28, 888-901.
39. Fischer, E.; Brossmer, R. Glycoconjugate J. 1995, 12, 707-713.
40. Anette Henriksen. Personal communication.
41. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal. Biochem 1970, 34, 595-598.
42. Pascal, R.; Sola, R. Tetrahedron Lett. 1998, 39, 5031-5034.
43. Meldal, M. Methods: A Companion to Methods Enzymol. 1994, 6, 417-424.