NMR studies on the conformation of oligomannosides and their interaction with banana lectin

Glycoconjugate Journal

Volumn 24, Issue 8, 2007, Pages 449-464

  Clavel, Caroline ^a   Canales, Angeles ^b   Gupta, Garima ^c   Santos, J Ignacio ^b   Cañada, F Javier ^b   Penadés, Soledad ^a   Surolia, Avadesha ^c   Jiménez Barbero, Jesús ^b  

^a CIC BIOMAGUNE   (Spain)

^b CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

^c INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Banana lectin; Mannose oligosaccharides; Molecular dynamics; Molecular recognition; NMR

Indexed keywords

MANNOSIDE; OLIGOMMANOSIDE DERIVATIVE; OLIGOSACCHARIDE; TETRASACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; BANANA; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SIMULATION; X RAY CRYSTALLOGRAPHY;

CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; MUSA; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OLIGOSACCHARIDES; PLANT LECTINS;

EID: 34848850789     PISSN: 02820080     EISSN: 15734986     Source Type: Journal    
DOI: 10.1007/s10719-007-9037-0     Document Type: Article

References (44)

1. Gabius, H.-J., Siebert, H.-C., Andre, S., Jimenez-Barbero, J., Rudiger, H.: Chemical biology of the sugar code. ChemBioChem 5, 740-764 (2004)
2. Ito, Y., Hagihara, S., Matsuo, I., Totani, K.: Structural approaches to the study of oligosaccharides in glycoprotein quality control. Curr. Opin. Struck. Biol. 15, 481-489 (2005)
3. Botos, I., Wlodawer, A.: Proteins that bind high-mannose sugars of the HIV envelope. Prog. Biophys. Mol. Biol. 88, 233-282 (2005)
4. See, for instance, Lam, S.N., Gervay-Hague, J.: Glycal scavenging in the synthesis of disaccharides using mannosyl iodide donors. J. Org. Chem. 70, 2387-2390 (2005)
5. Mandal, M., Dudkin, V.Y., Geng, X., Danishefsky, S.: In pursuit of carbohydrate-based HIV vaccines, Part 1: the total synthesis of hybrid-type gp120 fragments. Angew. Chem., Int. Ed. 43, 2557-2561 (2004)
6. Kiessling, L., Pontrello, J.K., Schuster, M.C.: Synthetic multivalent carbohydrate ligands as effectors or inhibitors of biological processes. In: Wong, C.-H. (ed.) Carbohydrate-based Drug Delivery, pp. 575-609. Wiley-VCH, Weinheim (2003)
7. Wang, L.X., Ni, J., Singh, S., Li, H.: Binding of high-mannose-type oligosaccharides and synthetic oligomannose clusters to human antibody 2G12: implications for HIV-1 vaccine design. Chem. Biol. 11, 127 (2004)
8. Barrientos, A.G., De la Fuente, J.M., Rojas, T.C., Fernández, A., Penadés, S.: Gold glyconanoparticles: synthetic polyvalent ligands mimicking glycocalyx-like surfaces as tools for glycobiological studies. Chem. Eur. J. 9, 1909-1921 (2003)
9. De la Fuente, J.M., Barrientos, A.G., Rojas, T.C., Rojo, J., Fernández, A., Penadés, S.: Gold glyconanoparticles as water-soluble polyvalent models to study carbohydrate interactions. Angew. Chem., Int. Ed. 40, 2257-2261 (2001)
10. de Souza, A.C., Halkes, K.M., Meeldijk, J.D., Verkleij, A.J., Vliegenthart, J.F.C., Kamerling, J.P.: Gold glyconanoparticles as probes to explore the carbohydrate-mediated self-recognition of marine sponge cells. ChemBioChem 6, 828-831 (2005)
11. Rojo, J., Díaz, V., de la Fuente, J., Segura, I., Barrientos, A.G., Riese, H.H., Bernad, A., Penadés, S.: Gold glyconanoparticles as new tools in antiadhesive therapy. ChemBioChem 5, 291-297 (2004)
12. Kogelberg, H., Solís, D., Jiménez-Barbero, J.: New structural insights into carbohydrate-protein interactions from NMR spectroscopy. Curr. Opin. Struck. Biol. 13, 646-653 (2003)
13. De la Fuente, J.M., Penadés, S.: Glyconanoparticles: types, synthesis and applications in glycoscience, biomedicine and material science. Biochim. Biophys. Acta 1760, 636-651 (2006)
14. Singh, D.D., Saikrishnan, K., Kumar, P., Dauter, Z., Sekar, K., Surolia, A., Vijayan, M.: Purification, crystallization and preliminary X-ray structure analysis of the banana lectin from Musa paradisiacal. Acta Crystallogr., D 60, 2104-2106 (2004)
15. Goldstein, I.J.: Lectin structure-activity: the story is never over. J. Agric. Food Chem. 50, 6583-6585 (2002)
16. Lee, H.-K., Scanlan, C.N., Huang, C.-Y., Chang, A.Y., Calarese, D.A., Dwek, R.A., Rudd, P.M., Burton, D.R., Wilson, I.A., Wong, C-H.: Reactivity-based one-pot synthesis of oligomannoses: defining antigens recognized by 2G12, a broadly neutralizing anti-HIV-1 antibody. Angew. Chem., Int. Ed. 43, 1000-1003 (2004)
17. Bax, A., Davis, D.G.: MLEV-17 based two-dimensional homonuclear magnetization transfer spectroscopy. J. Magn. Reson. 65, 355-360 (1985)
18. Kumar, A., Ernst, R.R., Wüthrich, K.: A two-dimensional nuclear overhauser enhancement (2D NOE) experiment for the elucidation of complete proton-proton cross-relaxation networks in biological macromolecules. Biochem. Biophys. Res. Commun. 95, 1-6 (1980)
19. Hwang, T.L., Shaka, A.J.: Cross relaxation without TOCSY: transverse rotating-frame overhauser effect spectroscopy. J. Am. Chem. Soc. 114, 3157-3158 (1992)
20. Bodenhausen, G., Reuben, D.J.: Natural abundance nitrogen-15 NMR by enhanced heteronuclear spectroscopy. Chem. Phys. Lett. 69, 185-189 (1980)
21. Stott, K., Stonehouse, J., Keeler, J., Hwang, T.L., Shaka, A.J.: Excitation sculpting in high-resolution nuclear magnetic resonance spectroscopy: application to selective NOE experiments. J. Am. Chem. Soc. 117, 4199-4200 (1995)
22. See, for instance, Asensio, J.L., Cañada, F.J., Khan, N., Mootoo, D.A., Jiménez-Barbero, J.: Conformational differences between O- and C-glycosides: the α-O-Man-(1→1)-β-Galα/-C-Man-(1→1)- β-Gal case-a decisive demonstration of the importance of the exo-anomeric effect on the conformation of glycosides. Chem. Eur. J. 6, 1035-1041 (2000)
23. Mayer, M., Meyer, B.: Group epitope mapping by saturation transfer difference NMR to identify segments of a ligand in direct contact with a protein receptor. J. Am. Chem. Soc. 123, 6108-6117 (2001)
24. Mohamadi, F., Richards, N.G.J., Guida, W.C., Liskamp, R., Lipton, M., Caufield, C., Chang, G., Hendrickson, T., Still, W.C.: MacroModel-an integrated software system for modeling organic and bioorganic molecules using molecular mechanics. J. Comput. Chem. 11, 440-467 (1990)
25. Allinger, N.L., Yuh, Y.H., Lii, J.H.: Molecular mechanics. The MM3 force field for hydrocarbons 1. J. Am. Chem. Soc. 111, 8551-8566 (1989)
26. Still, W.C., Tempzyk, A., Hawley, R., Hendrickson, T.: Semianalytical treatment of solvation for molecular mechanics and dynamics. J. Am. Chem. Soc. 112, 6127-6129 (1990)
27. Perez, S., Imberty, A., Engelsen, S., Gruza, J., Mazeau, K., Jimenez-Barbero, J., Poveda, A., Espinosa, J.F., van Eyck, B.P., Johnson, G., et al.: A comparison and chemometric analysis of several molecular mechanics force fields and parameter sets applied to carbohydrates. Carbohydr. Res. 314, 141-155 (1998)
28. Woods, R.J., Pathiaseril, A., Wormald, M.R., Edge, C.J., Dwek, R.A.: The high degree of internal flexibility observed for an oligomannose oligosaccharide does not alter the overall topology of the molecule. Eur. J. Biochem. 258, 372-386 (1998)
29. Gonzalez, L., Solis, D., Diaz-Mauriño, T., Bruix, M., Rico, M., Feizi, T., Jiménez-Barbero, J.: Conformational studies of the man8 oligosaccharide on native ribonuclease b and on the reduced and denatured protein. Arch. Biochem. Biophys. 383, 17-27 (2000)
30. Bernardi, A., Colombo, A., Sanchez-Medina, I.: Conformational analysis and dynamics of mannobiosides and mannotriosides using Monte Carlo/stochastic dynamics simulations. Carbohydr. Res. 339, 967-973 (2004)
31. Mari, S., Posteri, H., Marcou, G., Potenza, D., Micheli, F., Canada, F.J., Jimenez-Barbero, J., Bernardi, A.: Synthesis, conformational studies and mannosidase stability of a mimic of 1,2-mannobioside. Eur. J. Org. Chem. 24, 5119-5225 (2004)
32. Edge, C.J., Singh, U.C., Bazzo, R., Taylor, G.L., Dwek, R.A., Rademacher, T.W.: 500-Picosecond molecular dynamics in water of the Man.alpha.1.fwdarw. 2Man.alpha. glycosidic linkage present in Asn-linked oligomannose-type structures on glycoproteins. Biochemistry 29, 1971-1974 (1990)
33. Almond, A., Bunkenborg, J., Franch, T., Gotfredsen, C.H., Duus, J.O.: Comparison of aqueous molecular dynamics with NMR relaxation and residual dipolar couplings favors internal motion in a mannose oligosaccharide. J. Am. Chem. Soc. 123, 4792-4802 (2001)
34. Rutherford, T.J., Partridge, J., Weller, C.T., Homans, S.W.: Characterization of the extent of internal motions in oligosaccharides. Biochemistry 32, 12715-12724, (1993)
35. Almond, A., Duus, J.: Quantitative conformational analysis of the core region of N-glycans using residual dipolar couplings, aqueous molecular dynamics, and steric alignment. J. Biomol. NMR 20, 351-363 (2001)
36. Neuhaus, D., Williamson, M.P.: The Nuclear Overhauser Effect in Structural and Conformational Analysis. VCH, New York (1989)
37. Woods, R.J., Edge, C.J., Dwek, R.A.: Protein surface oligosaccharides and protein function. Nat. Struct. Mol. Biol. 1, 499-501 (1994)
38. Naidoo, K.J., Denysyk, D., Brady, J.W.: Molecular dynamics simulations of the N-linked oligosaccharide of the lectin from Erythrina corallodendron. Protein Eng. 10, 1249-1261 (1997)
39. Singh, D.D., Saikrishnan, K., Kumar, P., Surolia, A., Sekar, K., Vijayan, M.: Unusual sugar specificity of banana lectin from Musa paradisiaca and its probable evolutionary origin. Crystallographic and modelling studies. Glycobiology 15, 1025-1032 (2005)
40. Meagher, J.L., Winter, H.C., Ezell, P., Goldstein, I.J., Stuckey, J.A.: Crystal structure of banana lectin reveals a novel second sugar binding site. Glycobiology 15, 1033-1042 (2005)
41. Jiménez-Barbero, J., Peters, T.: NMR Spectroscopy of Glycoconjugates. VCH, Weinheim (2002)
42. Jayalakshmi, V., Biet, T., Peters, T., Krishna, N.R.: Refinement of the conformation of UDP-Galactose bound to galactosyltransferase using the STD NMR intensity-restrained CORCEMA optimization. J. Am. Chem. Soc. 126, 8610-8611 (2004)
43. Mari, S., Serrano-Gómez, D., Cañada, F.J., Corbí, A.L., Jiménez-Barbero, J.: 1D saturation transfer difference NMR Experiments on living cells: the DC-SIGN/Oligomannose interaction. Angew. Chem., Int. Ed. 44, 296-298 (2005)
44. Asensio, J.L., Espinosa, J.F., Dietrich, H., Cañada, F.J., Schmidt, R.R., Martin-Lomas, M., André, S., Gabius, H-J., Jiménez-Barbero, J.: Bovine heart galectin-1 selects a unique (Syn) conformation of C-lactose, a flexible lactose analogue. J. Am. Chem. Soc. 121, 8995-9000 (1999)