Significant other half of a glycoconjugate: Contributions of scaffolds to lectin-glycoconjugate interactions

Biochemistry

Volumn 53, Issue 27, 2014, Pages 4445-4454

  Talaga, Melanie L ^a   Fan, Ni ^a   Fueri, Ashli L ^a   Brown, Robert K ^a   Chabre, Yoann M ^a   Bandyopadhyay, Purnima ^a   Roy, Rene ^a   Dam, Tarun K ^a,b  

^a MICHIGAN TECHNOLOGICAL UNIVERSITY   (United States)

^b UNIVERSITÉ DU QUÉBEC À MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; ENTROPY; EPITOPES; POLYSACCHARIDES; PROTEINS;

BINDING PROPERTIES; COVALENT ATTACHMENT; LATTICE FORMATION; LECTIN RECOGNITION; LIMITING EFFECTS; PROTEIN SCAFFOLDS; SCAFFOLD STRUCTURES; SYNTHETIC SCAFFOLDS;

SCAFFOLDS (BIOLOGY);

EPITOPE; GLYCAN; GLYCOCONJUGATE; GLYCOPROTEIN; LECTIN;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; COVALENT BOND; CROSS LINKING; ENTROPY; IN VITRO STUDY; KINETICS; LECTIN BINDING; PRIORITY JOURNAL; PROTEIN CARBOHYDRATE INTERACTION; PROTEIN STRUCTURE; SURFACE CHARGE; THERMODYNAMICS;

CONCANAVALIN A; CROSS-LINKING REAGENTS; DENDRIMERS; GLYCOPROTEINS; KINETICS; MANNOSE; OLIGOSACCHARIDES; THERMODYNAMICS;

EID: 84904352739     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi5001307     Document Type: Article

References (47)

1. Chabre, Y. M. and Roy, R. (2010) Design and creativity in synthesis of multivalent neoglycoconjugates Adv. Carbohydr. Chem. Biochem. 63, 165-393
2. Chabre, Y. M. and Roy, R. (2013) Multivalent glycoconjugate syntheses and applications using aromatic scaffolds Chem. Soc. Rev. 42, 4657-4708
3. Kitov, P. I., Sadowska, J., Mulvey, M., Armstrong, G. D., Ling, H., Pannu, N. S., Read, R. J., and Bundle, D. R. (2000) Shiga-like toxins are neutralized by tailored multivalent carbohydrate ligands Nature 403, 669-672
4. Collins, M. N. and Birkinshaw, C. (2013) Hyaluronic acid based scaffolds for tissue engineering: A review Carbohydr. Polym. 92, 1262-1279
5. Turnbull, W. B. and Stoddart, J. F. (2002) Design and synthesis of glycodendrimers J. Biotechnol. 90, 231-255
6. Varki, A. (1993) Biological roles of oligosaccharides: All of the theories are correct Glycobiology 3, 97-130
7. Gabius, H.-J. (2006) Cell surface glycans: The why and how of their functionality as biochemical signals in lectin-mediated information transfer Crit. Rev. Immunol. 26, 43-79
8. Varki, A., Cummings, R. D., Esko, J. D., Freeze, H. H., Stanley, P., Bertozzi, C. R., Hart, G. W., and Etzler, M. E. (2009) Essentials of Glycobiology, 2nd ed., p 784, Cold Spring Harbor Laboratory Press, Plainview, NY.
9. Lundquist, J. J. and Toone, E. J. (2002) The cluster glycoside effect Chem. Rev. 102, 555-578
10. Dam, T. K. and Brewer, C. F. (2002) Thermodynamic studies of lectin-carbohydrate interactions by isothermal titration calorimetry Chem. Rev. 102, 387-429
11. Dam, T. K., Roy, R., Das, S. K., Oscarson, S., and Brewer, C. F. (2000) Binding of multivalent carbohydrates to concanavalin A and Dioclea grandiflora lectin. Thermodynamic analysis of the "multivalency effect" J. Biol. Chem. 275, 14223-14230
12. Mammen, M., Choi, S.-K., and Whitesides, G. M. (1998) Polyvalent interactions in biological systems: Implications for design and use of multivalent ligands and inhibitors Angew. Chem., Int. Ed. 37, 2754-2794
13. Dam, T. K., Gerken, T. A., Cavada, B. S., Nascimento, K. S., Moura, T. R., and Brewer, C. F. (2007) Binding studies of α-GalNAc-specific lectins to the α-GalNAc (Tn-antigen) form of porcine submaxillary mucin and its smaller fragments J. Biol. Chem. 282, 28256-28263
14. Cairo, C. W., Gestwicki, J. E., Kanai, M., and Kiessling, L. L. (2002) Control of Multivalent Interactions by Binding Epitope Density J. Am. Chem. Soc. 124, 1615-1619
15. Perrimon, N. and Bernfield, M. (2000) Specificities of heparan sulphate proteoglycans in developmental processes Nature 404, 725-728
16. Mammen, M., Dahmann, G., and Whitesides, G. M. (1995) Effective inhibitors of hemagglutination by influenza virus synthesized from polymers having active ester groups. Insight into mechanism of inhibition J. Med. Chem. 38, 4179-4190
17. Horan, N., Yan, L., Isobe, H., Whitesides, G. M., and Kahne, D. (1999) Nonstatistical binding of a protein to clustered carbohydrates Proc. Natl. Acad. Sci. U.S.A. 96, 11782-11786
18. Dam, T. K. and Brewer, C. F. (2008) Effects of clustered epitopes in multivalent ligand-receptor interactions Biochemistry 47, 8470-8476
19. Garner, O. B. and Baum, L. G. (2008) Galectin-glycan lattices regulate cell-surface glycoprotein organization and signaling Biochem. Soc. Trans. 36, 1472-1477
20. Grigorian, A., Torossian, S., and Demetriou, M. (2009) T-cell growth, cell surface organization, and the galectin glycoprotein lattice Immunol. Rev. 230, 232-246
21. Demetriou, M., Granovsky, M., Quaggin, S., and Dennis, J. W. (2001) Negative regulation of T-cell activation and autoimmunity by Mgat5 N-glycosylation Nature 409, 733-739
22. Gestwicki, J. E., Cairo, C. W., Strong, L. E., Oetjen, K. A., and Kiessling, L. L. (2002) Influencing Receptor-Ligand Binding Mechanisms with Multivalent Ligand Architecture J. Am. Chem. Soc. 124, 14922-14933
23. Chabre, Y. M., Brisebois, P., Abassi, L., Kerr, S., Fahy, J., Marcotte, I., and Roy, R. (2011) Hexaphenylbenzene as a rigid template for the straightforward syntheses of "star-shaped" glycodendrimers J. Org. Chem. 76, 724-727
24. Chabre, Y. M., Contino-Pépin, C., Placide, V., Shiao, T. C., and Roy, R. (2008) Expeditive synthesis of glycodendrimer scaffolds based on versatile TRIS and mannoside derivatives J. Org. Chem. 73, 5602-5605
25. Chabre, Y. M., Shiao, T. C., Vidal, S., and Roy, R. (2012) Synthesis of Prop-2-ynyl 2,3,4,6-tetra-O-acetyl-α- d -mannopyranoside. In Carbohydrate Chemistry: Proven Synthetic Methods (Kovac, P., Ed.) Vol. 1, Chapter 31, pp 275-278, CRC Press/Taylor & Francis Group, Boca Raton, FL.
26. Lis, H. and Sharon, N. (1978) Soybean agglutinin-a plant glycoprotein. Structure of the carboxydrate unit J. Biol. Chem. 253, 3468-3476
27. Mandal, D. K. and Brewer, C. F. (1992) Interactions of concanavalin A with glycoproteins: Formation of homogeneous glycoprotein-lectin cross-linked complexes in mixed precipitation systems Biochemistry 31, 12602-12609
28. Dubois, M., Gilles, K. A., Hamilton, J. K., Rebers, P. A., and Smith, F. (1951) A colorimetric method for the determination of sugars Nature 168, 167
29. Saha, S. K. and Brewer, C. F. (1994) Determination of the concentrations of oligosaccharides, complex type carbohydrates, and glycoproteins using the phenol-sulfuric acid method Carbohydr. Res. 254, 157-167
30. Goldstein, I. J. and Poretz, R. D. (1986) in The Lectins (Liener, I. E., Sharon, N., and Goldstein, I. J., Eds.) pp 35-244, Academic Press Inc., New York.
31. Wiseman, T., Williston, S., Brandt, J. F., and Lin, L.-N. (1989) Rapid measurement of binding constants and heats of binding using a new titration calorimeter Anal. Biochem. 179, 131-135
32. Bhattacharyya, L., Fant, J., Lonn, H., and Brewer, C. F. (1990) Binding and precipitating activities of Lotus tetragonolobus isolectins with l -fucosyl oligosaccharides. Formation of unique homogeneous cross-linked lattices observed by electron microscopy Biochemistry 29, 7523-7530
33. Gupta, D., Dam, T. K., Oscarson, S., and Brewer, C. F. (1997) Thermodynamics of lectin-carbohydrate interactions. Binding of the core trimannoside of asparagine-linked carbohydrates and deoxy analogs to concanavalin A J. Biol. Chem. 272, 6388-6392
34. Williams, B. D. and Lennarz, W. J. (1984) Control of asparagine-linked oligosaccharide chain processing: Studies on bovine pancreatic ribonuclease B. An in vitro system for the processing of exogenous glycoproteins J. Biol. Chem. 259, 5105-5114
35. Tai, T., Yamashita, K., Ogata-Arakawa, M., Koide, N., Muramatsu, T., Iwashita, S., Inoue, Y., and Kobata, A. (1975) Structural studies of two ovalbumin glycopeptides in relation to the endo-β-N-acetylglucosaminidase specificity J. Biol. Chem. 250, 8569-8575
36. Hiller, Y., Gershoni, J. M., Bayer, E. A., and Wilchek, M. (1987) Biotin binding to avidin. Oligosaccharide side chain not required for ligand association Biochem. J. 248, 167-171
37. Ziegler, F. D., Maley, F., and Trimble, R. B. (1988) Characterization of the glycosylation sites in yeast external invertase. II. Location of the endo-β-N-acetylglucosaminidase H-resistant sequins J. Biol. Chem. 263, 6986-6992
38. Mandal, D. K. and Brewer, C. F. (1993) Differences in the binding affinities of dimeric concanavalin A (including acetyl and succinyl derivatives) and tetrameric concanavalin A with large oligomannose-type glycopeptides Biochemistry 32, 5116-5120
39. Germain, R. N. and Stefanová, I. (1999) The dynamics of T cell receptor signaling: Complex orchestration and the key roles of tempo and cooperation Annu. Rev. Immunol. 17, 467-522
40. Weintraub, B. C., Jun, J. E., Bishop, A. C., Shokat, K. M., Thomas, M. L., and Goodnow, C. C. (2000) Entry of B cell receptor into signaling domains is inhibited in tolerant B cells J. Exp. Med. 191, 1443-1448
41. Sugiyama, J. E., Glass, D. J., Yancopoulos, G. D., and Hall, Z. W. (1997) Laminin-induced acetylcholine receptor clustering: An alternative pathway J. Cell Biol. 139, 181-191
42. Petrie, R. J., Schnetkamp, P. P., Patel, K. D., Awasthi-Kalia, M., and Deans, J. P. (2000) Transient translocation of the B cell receptor and Src homology 2 domain-containing inositol phosphatase to lipid rafts: Evidence toward a role in calcium regulation J. Immunol. 165, 1220-1227
43. Cochran, J. R., Aivazian, D., Cameron, T. O., and Stern, L. J. (2001) Receptor clustering and transmembrane signaling in T cells Trends Biochem. Sci. 26, 304-310
44. Kitano, H., Sumi, Y., and Tagawa, K. (2001) Recognition of novel lipopolypeptides with many pendent sugar residues by lectin Bioconjugate Chem. 12, 56-61
45. Hessler, G. and Baringhaus, K.-H. (2010) The scaffold hopping potential of pharmacophores Drug Discovery Today: Technol. 7, e263-e269
46. Endo, M. and Sugiyama, H. (2009) Chemical Approaches to DNA Nanotechnology ChemBioChem 10, 2420-2443
47. Straley, K. S., Wong, C., Foo, P., and Heilshorn, S. C. (2010) Biomaterial design strategies for the treatment of spinal cord injuries Journal of Neurotrauma 27, 1-19