Calcium-dependent carbohydrate-carbohydrate recognition between Lewis(x) blood group antigens

Angewandte Chemie - International Edition

Volumn 39, Issue 18, 2000, Pages 3246-3249

  Geyer, Armin ^a   Gege, Christian ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CALCIUM; CARBOHYDRATE; LACTOSE; LIGAND; LYMPHOCYTE ANTIGEN RECEPTOR; OLIGOSACCHARIDE; TRISACCHARIDE;

ARTICLE; BINDING AFFINITY; BLOOD GROUP LEWIS SYSTEM; CALCIUM TRANSPORT; CELL ADHESION; CELL MEMBRANE; CHEMICAL INTERACTION; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; COVALENT BOND; EUKARYOTIC CELL; LIGAND BINDING; MOLECULAR RECOGNITION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0034665614     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000915)39:18<3245::aid-anie3245>3.0.co;2-9     Document Type: Article

References (37)

1. a) R. A. Dwek, Chem. Rev. 1996, 96, 683-720;
2. b) S. Hakomori, Cancer Res. 1996, 56, 5309-5318.
3. a) I. Eggens, B. Fenderson, T. Toyokuni, B. Dean, M. Stroud, S. Hakomori, J. Biol. chem. 1989, 264, 9476-9484;
4. b) N. V. Bovin in Glycosciences (Eds.: H.-J. Gabius, S. Gahius), Chapman & Hall, Weinheim, 1997, 277-289;
5. c) S. Hakomori, K. Handa, K. Iwabuchi, S. Yamamura, A. Prinetti, Glycobiology 1998, 8, xi-xix;
6. d) B. G. Davis, J. Chem. Soc. Perkin I 1999, 3215-3237.
7. a) U. Dammer, O. Popescu, P. Wagner, D. Anselmetti, H.-J. Güntherodt, G. N. Misevic, Science 1995, 267, 1173-1175;
8. b) M. Mammen, S.-K. Choi, G. M. Whitesides, Angew. Chem. 1998, 110, 2908-2953; Angew. Chem. Int. Ed. 1998, 37, 2754-2794;
9. b) M. Mammen, S.-K. Choi, G. M. Whitesides, Angew. Chem. 1998, 110, 2908-2953; Angew. Chem. Int. Ed. 1998, 37, 2754-2794;
10. c) K. Matsura, A. Tsuchida, Y. Okahata, T. Akaike, K. Kobayashi, Bull. Cham. Soc. Jpn. 1998, 71, 2973-2977.
11. P. M. Macdonald, Acc. Chem. Res. 1997, 30, 196-207.
12. a) J. Vogel, G. Bendas, U. Bakowsky, G. Hummel, R. R. Schmidt, U. Kettmann, U. Rothe, Biochim. Biophys. Acta 1998, 1372, 205-215:
13. b) C. Gege, J. Vogel, G. Bendas, U. Rothe, R. R. Schmidt, Chem. Eur. J. 2000, 6, 111-122.
14. M. Boubelik, D. Floryk, J. Bohata, L. Draberova, J. Macak, F. Smid, P. Draher, Glycobiology 1998, 8, 139-146.
15. a) M. R. Wormald, C. J. Edge, R. A. Dwek, Biochem. Biophys. Res. Commun. 1991, 180, 1214-1221;
16. b) B. Henry, H. Desvaux, M. Pristchepa, P. Berthault, Y.-M. Zhang, J.-M. Mallet, J. Esnault, P. Sinay, Carbohydr. Res. 1999, 315, 48-62.
17. A. Geyer, C. Gege, R. R. Schmidt, Angew. Chem. 1999, 111, 1569-1571; Angew. Chem. Int. Ed. 1999, 38, 1466-1468.
18. A. Geyer, C. Gege, R. R. Schmidt, Angew. Chem. 1999, 111, 1569-1571; Angew. Chem. Int. Ed. 1999, 38, 1466-1468.
19. 1).
20. C. E. Bugg, J. Am. Chem. Soc. 1973, 95, 908-913; W. J. Cook, C. E. Bugg, Acta Crystallogr. Sect. B 1973, 29, 907-909.
21. C. E. Bugg, J. Am. Chem. Soc. 1973, 95, 908-913; W. J. Cook, C. E. Bugg, Acta Crystallogr. Sect. B 1973, 29, 907-909.
22. Higher affinities were observed for rigid pyranose rings with an ax-eq-ax arrangement of hydroxy groups. See: S. J. Angyal, Adv. Carbohydr. Chem. Biochem. 1989, 47, 1-43.
23. A. P. Davis, R. S. Wareham, Angew. Chem. 1999. 111, 3160-3179: Angew. Chem. Int. Ed. 1999, 39, 2978-2996.
24. A. P. Davis, R. S. Wareham, Angew. Chem. 1999. 111, 3160-3179: Angew. Chem. Int. Ed. 1999, 39, 2978-2996.
25. Compounds 1-4 were fully assigned by homo-and heteronuclear NMR methods. All NMR spectra were acquired at 600 MHz and 300 K.
26. Compensated ROESY spectra were acquired with a pulsed 4 kHz spin lock and a 200 ms mixing time. See: a) A. A. Bothner-By, R. L. Stephens, J. Lee, C. D. Warren, R. W. Jeanloz, J. Am. Chem. Soc. 1984, 106, 811-813;
27. b) A. Bax, D. G. Davis, J. Magn. Reson. 1985, 63, 207-213;
28. c) C. Griesinger, R. R. Ernst, J. Magn. Reson. 1987, 75, 261-271.
29. J. K. Beattie, M. T. Kelso, Aust. J. Chem. 1981, 34, 2563-2568.
30. 6-dependence of the NOE with isotropic tumbling of 4. See: A. Kumar, G. Wagner, R. R. Ernst, K. Wüthrich. J. Am. Chem. Soc. 1981, 103, 3654-3658.
31. 2) restraints in molecular dynamics simulations of 4. Structure sampling and energy minimization were carried out according to: Z.-H. Jiang, A. Geyer, R. R. Schmidt, Angew. Chem. 1995, 107, 2730-2734; Angew. Chem. Int. Ed. Engl. 1995, 34, 2520-2524. Figure 4 was drawn with SCHAKAL (E. Keller, University of Freiburg, Germany).
32. 2) restraints in molecular dynamics simulations of 4. Structure sampling and energy minimization were carried out according to: Z.-H. Jiang, A. Geyer, R. R. Schmidt, Angew. Chem. 1995, 107, 2730-2734; Angew. Chem. Int. Ed. Engl. 1995, 34, 2520-2524. Figure 4 was drawn with SCHAKAL (E. Keller, University of Freiburg, Germany).
33. The residual octahedral coordination sphere of calcium can be saturated by water. See: A. K. Katz, J. P. Glusker, S. A. Beebe, C. W. Bock, J. Am. Chem. Soc. 1996, 118, 5752-5763.
34. a) G. Siuzdak, Y. Ichikawa, T. J. Caulfield, B. Munoz, C.-H. Wong, K. C. Nicolaou, J. Am. Chem. Soc. 1993, 115, 2877-2881;
35. b) N. Kojima, B. A. Fenderson, M. R. Stroud, R. I. Goldberg, R. Habermann, T. Toyokuni, S. Hakomori, Glycoconjugate J. 1994, 11, 238-248.
36. R. P. Junghans, Immunology Today 1999, 20, 401-406.
37. x trisaccharide moiety is found in a well-defined solution conformation without populating secondary minima. A. Geyer. G. Hummel. T. Eisele, S. Reinhardt, R. R. Schmidt, Chem. Eur. J. 1996, 2, 981-988.