Man α1-2 Man α-OMe-concanavalin A complex reveals a balance of forces involved in carbohydrate recognition

Glycobiology

Volumn 9, Issue 6, 1999, Pages 539-545

  Moothoo, Davina N ^a   Canan, Booma ^a   Field, Robert A ^a   Naismith, James H ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

Carbohydrate conformation; Con A saccharide complex; Crystal structure; Molecular recognition

Indexed keywords

CONCANAVALIN A; DISACCHARIDE; MANNOSE; METHYLGLYCOSIDE; MONOSACCHARIDE; TETRAMER; CARBOHYDRATE; DRUG DERIVATIVE; MANNOSYL(1 2) MANNOSYL METHYL ESTER CONCANAVALIN A COMPLEX; MANNOSYL(1-2)-MANNOSYL METHYL ESTER CONCANAVALIN A COMPLEX;

ARTICLE; BINDING SITE; CRYSTAL STRUCTURE; PRIORITY JOURNAL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HYDROGEN BOND;

CARBOHYDRATE CONFORMATION; CARBOHYDRATES; CONCANAVALIN A; HYDROGEN BONDING; MODELS, MOLECULAR;

EID: 0032586737     PISSN: 09596658     EISSN: None     Source Type: Journal    
DOI: 10.1093/glycob/9.6.539     Document Type: Article

References (32)

1. Bains, G., Lee, R.T., Lee, Y.C. and Freire, E. (1992) Microcalorimetric study of wheat-germ-agglutinin binding to N-acetylglucosamine and its oligomers. Biochemistry, 31, 12624-12628.
2. Bains, G., Xie, D., Wang, R.J. and Freire, E. (1993) Structural thermodynamic parametrization of the energetics of protein-carbohydrate interactions. Biophys. J., 64, A 166.
3. Brunger, A.T. and Adams, P.D. (1998) CNS: crystallography and NMR system, development version 0.1.
4. (1994) The CCP4 suite: programs for protein crystallography. Acta Crystallogr. D, 50, 760-763.
5. Chervenak, M.C. and Toone, E.J. (1995) Calorimetric analysis of the binding of lectins with overlapping carbohydrate-binding ligand specificities. Biochemistry, 34, 5685-5695.
6. Chervenak, M.C. and Toone, E.J. (1996) Analysis of the binding specificities of oligomannoside-binding proteins using methylated monosaccharides. Bioorganic Med. Chem., 4, 1963-1977.
7. Deacon, A., Gleichmann, T., Kalb (Gilboa), A.J., Price, H., Rafferty, J., Bradbrook, G., Yariv, J. and Helliwell, J.R. (1997) The structure of concanavalin A and its bound solvent structure determined with small molecule accuracy at 0.94 Å resolution. J. Chem. Soc. Faraday Trans., 53, 4305-4312.
8. Derewenda, Z., Yariv, J., Helliwell, J.R., Kalb, A.J., Dodson, E.J., Papiz, M.Z., Wan, T. and Campbell, J. (1989) The structure of the saccharide-binding site of concanavalin-a. EMBO J., 8, 2189-2193.
9. Dowd, M.K., French, A.D. and Reilly, P.J. (1995) Molecular mechanics modeling of alpha-(1-2)-linked, alpha-(1-3)-linked, and alpha-(1-6)-linked mannosyl disaccharides with MM3. Carbohydr. Chem., 14, 589-600.
10. Dwek, R.A. (1996) Glycobiology: towards understanding the function sugars. Chem. Rev., 96, 683-720.
11. Elgavish, S. and Shaanan, B. (1997) Lectin-carbohydrate interactions: different folds, common recognition principles. Trends Biochem. Sci., 22, 462-467.
12. Engh, R.A. and Huber, R. (1991) Accurate bond and angle parameters for x-ray protein structure refinement. Acta Crystallogr. A, 47, 392-400.
13. Goldstein, I.J. (1975) Studies on the combining sites of concanavalin A. Adv. Exp. Med. Biol., 55, 35-53.
14. Goldstein, I.J., Reichert, C.M. and Misaki, A. (1974) Interaction of concanavalin A with model substrates. Ann. NY Acad. Sci., 234, 283-295.
15. Harrop, S.J., Helliwell, J.R., Wan, T.C.M., Kalb, A.J., Tong, L. and Yariv, J. (1996) Structure solution of a cubic-crystal of concanavalin a complexed with methyl alpha-D-glucopyranoside. Acta Crystallogr. D, 52, 143-155.
16. Jones, T.A., Zou, J.-Y., Cowan, S.W. and Kjeldgaard, M. (1991) Improved methods for building protein models in electron density maps and the location of errors in these models. Acta Crystallogr. A, 47, 110-119.
17. Laskowski, R.A., McArthur, M.W., Moss, D.S. and Thornton, J.M. (1993) PROCHECK: a program to check the stereochemical quality of protein structures. J. Appl. Cryst., 26, 283.
18. Loris, R., Maes, D., Poortmans, F., Wyns, L. and Bouckaert., J (1996) A structure of the complex between concanavalin A and methyl-3,6-di-O-(alpha-D-mannopyranosyl)-alpha-D-mannopyranoside reveals two binding modes. J. Biol. Chem., 1996, 271, 30614-30618.
19. Loris, R., Hamelryck, T., Bouckaert, J. and Wyns, L. (1998) Legume lectin structure. Biochem. Biophys. Acta, 1383, 9-36.
20. Mandal, D.K., Kishore, N. and Brewer, C. F. (1994) Thermodynamics of lectincarbohydrate interactions - titration microcalorimetry measurements of the binding of N-linked carbohydrates and ovalbumin to concanavalin A. Biochemistry, 33, 1149-1156.
21. Merrit, E.A. and Murphy, M.E.P. (1994) Raster 3D version 2.0: a program for photorealistic graphics. Acta Crystallogr. D, 50, 869-873.
22. Moothoo, D.N. and Naismith, J.H. (1998) Concanavalin A distorts the β-GlcNAc-(1-2)-Man linkage of β-GlcNAc-(1-2)-α-Man-(1-3)-[β-GLcNAc-(1 -2)-α-Man-(1-6)]-Man upon binding. Glycobiology, 8, 173-181.
23. Moothoo, D.N. and Naismith, J.H. (1999) A general method for co-crystallisation of concanavalin A with carbohydrates. Acta Crystallogr. D, 55, 353-355.
24. Naismith, J.H. and Field, R.A. (1996) Structural basis of trimannoside recognition by concanavalin-a. J. Biol. Chem., 271, 972-976.
25. Naismith, J.H., Emmerich, C., Habash, J., Harrop, S.J., Helliwell, J.R., Hunter, W.N., Raftery, J., Kalb, A.J. and Yariv, J. (1994) Refined structure of concanavalin-a complexed with methyl alpha-D-mannopyranoside at 2.0 angstrom resolution and comparison with the saccharide-free structure. Acta Crystallogr. D, 50, 847-858.
26. Navaza, J. (1994) AMoRe: an automated package for molecular replacement. Acta Crystallogr. A, 50, 157-163.
27. Ogawa, T., Katano, K., Sasajima, K. and Matsui, M. (1981) Synthetic studies on cell-surface glycans. 3. Branching pentasaccharides of glycoprotein. Tetrahedron, 37, 2779-2786.
28. Perez, S., Meyer, C. and Imberty, A. (1995) Practical tools for accurate modelling of complex carbohydrates and their interactions with proteins. In Pullman, A., Jortner, J., and Pullman, B. (eds.), Modelling of Biomolecular Structures and Mechanisms. Kluwer Academic, Dordrecht, pp. 425-454.
29. Peters, T. (1991) Synthesis and conformational-analysis of methyl 2-o-(alpha-D-mannopyranosyl)-alpha-D-mannopyranoside. Liebigs Ann. Chem., 2, 135-141.
30. Srikrishnan, T., Chowdhary, M.S. and Matta K.L. (1989) Crystal and molecularstructure of methyl o-alpha-D-manno-pyranosyl-(1-2)-alpha-D-mannopyranoside. Carbohydr. Res., 186, 167-175.
31. Toone, E.J. (1994) Structure and energetics of protein carbohydrate complexes. Curr. Opin. Struct. Biol., 4, 719-728.
32. Weatherman, R.V., Mortell, K.I., Chervenak, M., Kiessling, L.L. and Toone, E.J. (1996) Specificity of C-glycoside complexation by mannose glucose specific lectins. Biochemistry, 35, 3619-3624.