Antithrombin-binding octasaccharides and role of extensions of the active pentasaccharide sequence in the specificity and strength of interaction: Evidence for very high affinity induced by an unusual glucuronic acid residue

Journal of Biological Chemistry

Volumn 283, Issue 39, 2008, Pages 26662-26675

  Guerrini, Marco ^a   Guglieri, Sara ^a   Casu, Benito ^a   Torri, Giangiacomo ^a   Mourier, Pierre ^b   Boudier, Christian ^c   Viskov, Christian ^b  

^a Istituto di Ricerche Chimiche e Biochimiche G Ronzoni   (Italy)

^b SANOFI   (France)

^c CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; AFFINITY CHROMATOGRAPHY; CARBOXYLIC ACIDS; CHROMATOGRAPHIC ANALYSIS; CHROMATOGRAPHY; FLOW INTERACTIONS; GLUCOSE; IONIZATION OF LIQUIDS; LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; ORGANIC POLYMERS; POLYSACCHARIDES; SIZE EXCLUSION CHROMATOGRAPHY; VOLUMETRIC ANALYSIS;

ANTITHROMBIN; ANTITHROMBOTIC; FLUORESCENCE TITRATIONS; GLUCURONIC ACIDS; HIGH AFFINITIES; HIGH PURITIES; HYDROXYL GROUPS; IONIC INTERACTIONS; MOLECULAR CONFORMATIONS; NONIONIC INTERACTIONS; PENTASACCHARIDE; REDUCING ENDS; SIZE EXCLUSIONS; URONIC ACIDS;

HIGH PRESSURE LIQUID CHROMATOGRAPHY;

ANTITHROMBIN; ENOXAPARIN; IDURONIC ACID; LOW MOLECULAR WEIGHT HEPARIN; OCTASACCHARIDE DERIVATIVE; PENTASACCHARIDE; POLYSACCHARIDE; UNCLASSIFIED DRUG; URONIC ACID; ANTITHROMBIN III; OLIGOSACCHARIDE;

AFFINITY CHROMATOGRAPHY; ANTIBODY AFFINITY; ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; CONTROLLED STUDY; DISSOCIATION CONSTANT; GEL PERMEATION CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR INTERACTION; MOLECULAR MODEL; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; TITRIMETRY; CHEMISTRY; HUMAN; ISOLATION AND PURIFICATION; LIQUID CHROMATOGRAPHY; METABOLISM; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYSIOLOGY; PROTEIN BINDING;

ANTITHROMBIN III; CARBOHYDRATE CONFORMATION; CHROMATOGRAPHY, LIQUID; HEPARIN, LOW-MOLECULAR-WEIGHT; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; OLIGOSACCHARIDES; PROTEIN BINDING;

EID: 55549136766     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M801102200     Document Type: Article

References (40)

1. Hoppensteadt, D., Iqbal, O., and Fareed, J. (2005) in Chemistry and Biology of Heparin and Heparan Sulfate (Garg, H. G., Linhardt, R. J., and Hales, C. A., eds) pp. 583-606, Elsevier Ltd., Oxford, UK
2. Thunberg, L., Bäckström, G., and Lindahl, U. (1982) Carbohydr. Res. 100, 393-410
3. Petitou, M., and van Boeckel, C. A. A. (2004) Angew. Chem. Int. Ed. 43, 3118-3133
4. Casu, B. (2005) in Chemistry and Biology of Heparin and Heparan Sulphate (Garg, H. G., Linhardt, R. J., and Hales, C. A., eds) pp. 1-28, Elsevier Ltd., Oxford, UK
5. Casu, B., and Lindahl, U. (2001) Adv. Carbohydr. Chem. Biochem. 57, 159-206
6. de Kort, M., Buijsman, R. C., and van Boeckel, C. A. (2005) Drug Discov. Today 10, 769-779
7. Linhardt, R. J., and Gunay, N. S. (1999) Semin. Thromb. Hemostasis 25, 5-16
8. Toida, T., Hileman, R. E., Smith, A. E., Vlahova, P. I., and Linhardt, R. J. (1996) J. Biol. Chem. 271, 32040-32047
9. Loganathan, D., Wang, H. M., Mallis, L. M., and Linhardt, R. J. (1990) Biochemistry 29, 4362-4368
10. Guerrini, M., Guglieri, S., Beccati, D., Torri, G., Viskov, C., and Mourier, P. (2006) Biochem. J. 399, 191-198
11. Belzar, K. J., Dafforn, T. R., Petitou, M., Carrell, R. W., and Huntington, J. A. (2000) J. Biol. Chem. 275, 8733-8741
12. Jin, L., Abrahams, J. P., Skinner, R., Petitou, M., Pike, R. N., and Carrell, R. W. (1997) Proc. Natl. Acad. Sci. U. S. A. 94, 14683-14688
13. Johnson, D. J., Li, W., Adams, T. E., and Huntington, J. A. (2006) EMBO J. 25, 2029-2037
14. Li, W., Johnson, D. J., Esmon, C. T., and Huntington, J. A. (2004) Nat. Struct. Mol. Biol. 11, 857-862
15. Hricovini, M., Guerrini, M., Bisio, A., Torri, G., Petitou, M., and Casu, B. (2001) Biochem. J. 359, 265-272
16. Ragazzi, M., Ferro, D. M., and Provasoli, M. (1986) J. Comput. Chem. 7, 105-112
17. Casu, B., and Torri, G. (1999) Semin. Thromb. Hemostasis 25, 17-26
18. Boudier, C., and Bieth, J. G. (2001) Biochemistry 40, 9962-9967
19. Mourier, P. A. J., and Viskov, C. (2004) Anal. Biochem. 332, 299-313
20. Höök, M., Björk, I., Hopwood, J., and Lindahl, U. (1976) FEBS Lett. 66, 90-93
21. Olson, S., and Shore, J. (1981) J. Biol. Chem. 256, 11065-11072
22. Olson, S., Björk, I., Sheffer, R., Craig, P., Shore, J., and Choay, J. (1992) J. Biol. Chem. 267, 12528-12538
23. Huntington, J. A., Olson, S. T., Fan, B., and Gettins, P. G. W. (1996) Biochemistry 35, 8495-8503
24. Desai, U. R., Petitou, M., Bjork, I., and Olson, S. T. (1998) J. Biol. Chem. 273, 7478-7487
25. Lin, P., Sinha, U., and Betz, A. (2001) Biochim. Biophys. Acta 1526, 105-113
26. Morris, G. M., Goodsell, D. S., Halliday, R. S., Huey, R., Hart, W. E., Belew, R., and Olson, A. J. (1998) J. Comput. Chem. 19, 1639-1662
27. Moseley, H. N. B., Curto, E. V., and Krishna, N. R. (1995) J. Magn. Reson. 108, 243-261
28. Angulo, J., Hricovíni, M., Gairi, M., Guerrini, M., de Paz, J. L., Ojeda, R., Martín-Lomas, M., and Nieto, P. M. (2005) Glycobiology 15, 1008-1015
29. Record, M. T., Jr., Lohman, M. L., and De Haseth, P. (1976) J. Mol. Biol. 107, 145-158
30. Olson, S. T., and Bjork, I. (1991) J. Biol. Chem. 266, 6353-6364
31. Hjelm, R., and Schedin-Weiss, S. (2007) Biochemistry 46, 3378-3384
32. Olson, S. T., Halvorson, H. R., and Björk, I. (1991) J. Biol. Chem. 266, 6342-6352
33. Thompson, L. D., Pantoliano, M. W., and Springer, B. A. (1994) Biochemistry 33, 3831-3840
34. Hileman, R. E., Jennings, R. N., and Linhardt, R. J. (1998) Biochemistry 37, 15231-15237
35. Ragazzi, M., Ferro, D. R., Provasoli, A., Pumilia, P., Cassinari, A., Torri, G., Guerrini, M., Casu, B., Nader, H. B., and Dietrich, C. P. (1993) J. Carbohydr. Chem. 12, 523-535
36. Mayer, M., and Meyer, B. (1999) Angew. Chem. Int. Ed. 38, 1784-1788
37. Mayer, M., and Meyer, B. (2001) J. Am. Chem. Soc. 123, 6108-6117
38. Seyrek, E., Dubin, P. L., and Henriksen, J. (2007) Biopolymers 86, 249-259
39. Verli, H., and Guimarães, J. A. (1997) J. Mol. Graph. Model. 15, 18-36
40. Guerrini, M., Guglieri, S., Naggi, A., Sasisekharan, R., and Torri, G. (2007) Semin. Thromb. Hemostasis 33, 478-487