Fluorescence spectrometry in studies of carbohydrate-protein interactions

Journal of Biochemistry

Volumn 121, Issue 5, 1997, Pages 818-825

  Lee, Yuan C ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

Conformation; Energy transfer; Glycopeptides; Substrates

Indexed keywords

CARBOHYDRATE; CARBOHYDRATE BINDING PROTEIN; GLYCOPEPTIDE; PROTEIN; TRYPTOPHAN;

ANISOTROPY; ENERGY TRANSFER; FLUORESCENCE; LIGAND BINDING; MOLECULAR INTERACTION; POLARIZATION; PROTEIN BINDING; PROTEIN STRUCTURE; REVIEW; SPECTROFLUOROMETRY;

EID: 0030959108     PISSN: 0021924X     EISSN: None     Source Type: Journal    
DOI: 10.1093/oxfordjournals.jbchem.a021658     Document Type: Review

References (66)

1. Stryer, L. (1978) Fluorescence energy transfer as a spectroscopic ruler. Annu. Rev. Biochem. 47, 819-846
2. Lakowicz, J.R. (1983) Principles of Fluorescence Spectroscopy, Plenum Press, New York, NY
3. Bennett, J.P., Jr. and Yamamura, H.I. (1985) Neurotransmitter, hormone, or drug receptor binding methods in Neurotransmitter Receptor Binding (Yamamura, H.I., Enna, S.J., and Kuhar, M.J., eds.) 2nd ed., pp. 61-89, Rven Press, New York, NY
4. Glaudemans, C.P.J. (1980) Methods for measuring the affinity between carbohydrate ligands and certain proteins. Methods Carbohydr. Chem. 8, 145-149
5. Khan, M.I., Sastry, M.V., and Surolia, A. (1986) Thermodynamic and kinetic analysis of carbohydrate binding to the basic lectin from winged bean (Psophocarpus tetragonolobus). J. Biol. Chem. 261, 3013-3019
6. Brown, M.P., Shaikh, N., Brenowitz, M., and Brand, L. (1994) The allosteric interaction between D-galactose and the Escherichia coli galactose repressor protein. J. Biol. Chem. 269, 12600-12605
7. Nashed, E.M. and Glaudemans, C.P.J. (1996) Observation on the binding of four anti-carbohydrate monoclonal antibodies to their homologous ligands. J. Biol. Chem. 271, 8209-8214
8. Munson, P.J. and Rodbard, D. (1980) LIGAND: A versatile computerized approach for characterization of ligand-binding systems. Anal. Biochem. 107, 220-239
9. Johnson, M.L. and Fraunt, L.M. (1992) Parameter estimation by least square methods. Methods Enzymol. 210, 1-37
10. Lotan, R. and Sharon, N. (1973) The fluorescence of wheat germ agglutinin and of its complexs with saccharides. Biochem. Biophys. Res. Commun. 55, 1340-1350
11. Chapman, D.M., Grisaro, V., and Sharon, N. (1967) The binding of oligosaccharides containing N-acetylglucosamine and N-acetylmuramic acid to lysozyme. J. Biol. Chem. 242, 4388-4394
12. Jolley, M.E. and Glaudemans, C.P.J. (1974) The determination of binding constants for binding between carbohydrate ligands and certain proteins. Carbohydr. Res. 33, 377-382
13. Glaudemans, C.P.J. and Kovac, P. (1988) Deoxygluoro carbohydrates as probes of binding sites of monoclonal antisaccharide antibodies in Fluorinated Carbohydrates. Chemical and Biochemical Aspects (Taylor, N.F., ed.) Vol. 374, pp. 78-108, Amer. Chem. Soc., Washington, DC
14. Goldstein, I.J., Blake, D.A., Ebisu, S., Williams, T.J., and Murphy, L.A. (1981) Carbohydrate binding studies on the Bandeiraea simplicifolia I isolectins. Lectins which are mono-, di-, tri-, and tetravalent for N-acetyl-D-galactosamine. J. Biol. Chem. 256, 3890-3893
15. Loontiens, F.G., Clegg, R.M., Van Landschoot, A., and Jovin, T. M. (1977) Binding of 4-methylumbelliferyl alpha-D-mannopyranoside to tetrameric concanavalin A. Fluorescence temperature-jump relaxation study. Eur. J. Biochem. 78, 465-469
16. Puri, K.D., Khan, M.I., Gupta, D., and Surolia, A. (1993) Thermodynamic and kinetic studies on the mechanism of binding of methylumbelliferyl galactosides to the basic agglutinin from winged bean (Psophocarpus tetragonolobus). J. Biol. Chem. 268, 16378-16387
17. De Boeck, H., Loontiens, F.G., Lis, H., and Sharon, N. (1984) Binding of simple carbohydrates and some N-acetyllactosamine-containing oligosaccharides to Erythrina cristagalli agglutinin as followed with a fluorescent indicator ligand. Arch. Biochem. Biophys. 234, 297-304
18. Freifelder, D. (1982) Fluorescence spectroscopy in Physical Biochemistry. Application to Biochemistry and Molecular Biology, pp. 537-572, W.H. Freeman, Co., San Francisco, CA
19. Khan, M.I., Mathew, M.K., Balaram, P., and Surolia, A. (1980) Fluorescence-polarization studies on binding of 4-methylumbelliferyl β-D-galactopyranoside to Ricinus communis (castor bean) agglutinin. Biochem. J. 191, 395-400
20. Khan, M.I., Surolia, N., Mathew, M.K., Balaram, P., and Surolia, A. (1981) Fluorescence polarization as a tool to study lectin-sugar interaction. An investigation of the binding of 4-methylumbelliferyl β-D-galactopyranoside to Abrus precatorious agglutinin. Eur. J. Biochem. 115, 149-152
21. Houston, L.L. and Dooley, T.P. (1982) Binding of two molecules of 4-methylumbelliferyl galactose or 4-methylumbelliferylgalactosamine to the B chains of ricin and Ricinus communis agglutinin and to purified ricin B chain. J. Biol. Chem. 257, 4147-4151
22. Welply, J.K., Abbas, S.Z., Scudder, P., Keene, J.L., Broschat, K., Casnocha, S., Gorka, C., Steininger, C., Howard, S.C., Schmuke, J.J., Graneto, M., Rotsaert, J.M., Manger, I.D., and Jacobs, G.S. (1994) Multivalent sialyl-LeX: potent inhibitors of E-selectin-mediated cell adhesion; reagent for staining activated endothelial cells. Glycobiology 4, 259-265
23. Lemieux, R.U., Bock, K., Kato, S., and Rao, V.S. (1980) The conformation of oligosaccharides related to the ABH and Lewis human blood group determinants. Can. J. Chem. 58, 631-653
24. Bock, K., Arnarp, J., and Lönngren, J. (1982) The preferred conformation of oligosaccharides derived from the complex-type carbohydrate portions of glycoproteins. Eur. J. Biochem. 129, 171-178
25. Lee, Y.C., Townsend, R.R., Hardy, M.R., Lonngren, J., and Bock, K. (1984) Binding of synthetic clustered ligands to the Gal/ GalNAc lectin on isolated rabbit hepatocytes in Biochemical and Biophysical Studies of Proteins and Nucleic Acids (Lo, T.-P., Liu, T.-Y., and Li, C.-H., eds.) pp. 349-360, Elsevier, New York, NY
26. Lakowicz, J.R. (1983) Principles of Fluorescence Spectroscopy, Plenum Press, New York, NY
27. Wu, P. and Brand, L. (1994) Resonance energy transfer: Methods and application. Anal. Biochem. 281, 1-13
28. Rice, K.G., Wu, P., Brand, L., and Lee, Y.C. (1991) Interterminal distance and flexibility of a triantennary glycopeptide as measured by resonance energy transfer. Biochemistry 30, 6646-6655
29. Lee, Y.C. (1992) Biochemistry of carbohydrate-protein interactions. FASEB J. 6, 3193-3200
30. Wu, P., Rice, K.G., Brand, L., and Lee, Y.C. (1991) Differential flexibilities in three branches of an N-linked triantennary glycopeptide. Proc. Natl. Acad. Sci. USA 88, 9355-9359
31. Rice, K.G., Wu, P., Brand, L., and Lee, Y.C. (1993) Modification of oligosaccharide antenna flexibility induced by exoglycosidase trimming. Biochemistry 32, 7264-7270
32. Lee, K.B. and Lee, Y.C. (1996) Conformational studies of glycopeptides by energy transfer. Introduction of fluorophore at specific branches of biantennary glycopeptides. J. Biol. Chem. 271, 1462-1469
33. Lee, K.B., Matsuoka, K., Nishimura, S., and Lee, Y.C. (1995) A new approach to assay endo-type carbohydrases: Bifluorescent-labeled substrates for glycoamidases and ceramide glycanases. Anal. Biochem. 230, 31-36
34. Wu, P., Lee, K.B., Brnad, L., and Lee, Y.C. (1996) Solution conformations of a biantennary glycopeptide and a series of its exoglycosidase products from sequential trimming of sugar residues. J. Biol. Chem. 271, 1470-1474
35. Stubbs, H.J., Lih, J.J., Gustafson, T.L., and Rice, K.G. (1996) Influence of core fucosylation on the flexibility of a biantennary N-linked oligosaccharide. Biochemistry 35, 937-947
36. Imperiali, B. and Rickert, K.W. (1995) Conformational implications of asparagine-linked glycosylation. Proc. Natl. Acad. Sci. USA 92, 97-101
37. Payre, N., Cottaz, S., and Driguez, H. (1995) Chemoenzymatic synthesis of a modified pentasaccharide as a specific substrate for a sensitive assay of α-amylase by fluorescence quenching. Angew. Chem. Int. Ed. Engl. 34, 1239-1241
38. Ferro, V., Meldal, M., and Bock, K. (1994) Synthesis of 2′-and 2′-O-acylated maltotriosides as potential fluorescence-quenched substrates for α-amylase. J. Chem. Soc. Perkins Trans. I, 2169-2176
39. Matsuoka, K., Nishimura, S., and Lee, Y.C. (1994) Synthesis of bi-fluorescence-labeled lactposide: A substrate for continual assay of ceramide glycanase. Tetrahedron: Assymetry 5, 2335-2338
40. Matsuoka, K., Nishimura, S., and Lee, Y.C. (1995) A bi-fluorescence-labeled substrate for ceramide glycanase based on fluorescence energy transfer. Carbohydr. Res. 276, 31-42
41. Li, S.-C., DeGasperi, R., Muldrey, J.E., and Li, Y.-T. (1986) A unique glycosphingolipid-splitting enzyme (ceramide-glycanase from leech) cleaves the linkage between the oligosaccharide and the ceramide. Biochem. Biophys. Res. Commun. 141, 346-352
42. Rice, K.G., Wu, P., Brand, L., and Lee, Y.C. (1993) Modification of oligosaccharide antenna flexibility induced by exoglycosidase trimming. Biochemistry 32, 7264-7270
43. Gomez, F.A., Avila, L.Z., Chu, Y.-H., and Whiteside, G.M. (1994) Determination of binding constants of ligands to proteins by affinity capillary electrophoresis: Compensation for electoosmotic flow. Anal. Chem. 66, 1785-1791
44. Shimura, K. and Kasai, K. (1995) Determination of the affinity constants of concanavalin A for monosaccharides by fluorescence affinity probe capillary electrophoresis. Anal. Biochem. 227, 186-194
45. Heegaard, N.H. and Robey, F.A. (1992) Use of capillary zone electrophoresis to evaluate the binding of anionic carbohydrates to synthetic peptides derived from human serum amyloid P component. Anal. Chem. 64, 2479-2482
46. 2+ and phosphorylcholine to human C-reactive protein. J. Immunol. Methods 166, 103-110
47. Lee, K.B., Kim, Y.S., and Linhardt, R.J. (1992) Lectin affinity electrophoresis for the separation of fluorescently labeled sugar derivatives. Anal. Biochem. 203, 206-210
48. Linhardt, R.J., Han, X.-J., and Fromm, J.R. (1995) Lectin affinity electrophoresis. Mol. Biotechnol. 3, 191-197
49. Lee, Y.C. and Lee, R.T. (1994) Enhanced biochemical affinities of multivalent neoglycoconjugates in Neoglycoconjugates: Preparation and Applications (Lee, Y.C. and Lee, R.T., eds.) pp. 23-50, Academic Press, San Diego, CA
50. Nagata, K., Furuike, T., and Nishimura, S. (1995) Fluorescence-labeled synthetic glycopolymers: a new type of sugar ligands of lectins. J. Biochem. 118, 278-284
51. Lee, R.T. and Lee, Y.C. (1979) Preparation of 1-thioglycosides having ω-aldehydo aglycons useful for attachment to proteins by reductive animation. Carbohydr. Res. 77, 149-156
52. Eichler, E., Kihlberg, J., and Bundle, D.R. (1991) Access to fluorescent probes via allyl glycosides: the synthesis of a Brucella trisaccharide epitope linked to a coumarin. Glycoconj. J. 8, 69-74
53. De Boeck, Lis, H., van Tilbeurgh, H., Sharon, N., and Loontiens, F.G. (1984) Binding of simple carbohydrates and some of their chromophoric derivatives to soybean agglutinin as followed by titrimetric procedures and stopped flow kinetics. J. Biol. Chem. 259, 7067-7074
54. De Boeck, H., Macgregor, R.B., Jr., Clegg, R.M., Sharon, N., and Loontiens, F.G. (1985) Binding of N-dansylgalaetosamine to the lectin from Erythrina cristagalli as followed by stopped-flow and pressure-jump relaxation kinetics. Eur. J. Biochem. 149, 141-145
55. Sastry, M.V., Banarjee, P., Patanjali, S.R., Swamy, M.J., Swarnalatha, G.V., and Surolia, A. (1986) Analysis of saccharide binding to Artocarpus integrifolia lectin reveals specific recognition of T-antigen (β-D-Gal(1-3)D-GalNAc). J. Biol. Chem. 261, 11726-11733
56. Kallin, E. (1994) Use of aminoalditols and glycosylamines in neoglycoconjugate synthesis in Neoglycoproteins: Preparation and Applications (Lee, Y.C. and Lee, R.T., eds.) pp. 199-223, Academic Press, San Diego, CA
57. Rasmussen, J.R. and Davis, J. (1992) Identification and derivatization of (oligosaccharyl)amines obtained by treatment of asparagine-linked glycopeptides with N-GLYCANASE enzyme. J. Am. Chem. Soc. 114, 1124-1126
58. Manger, I.D., Wong, S.Y.C., Rademacher, T.W., and Dwek, R.A. (1992) Synthesis of 1-N-glycyl β-oligosaccharide derivatives. Reactivity of Lens culinaris lectin with a fluorescent labeled streptavidin pseudoglycoprotein and immobilized neoglycolipid. Biochemistry 31, 10733-10740
59. Lee, R.T. and Lee, Y.C. (1986) Preparation of a high-affinity photolabeling reagent for the Gal/GalNAc lectin of mammalian liver: Demonstration of galactose-combining sites on each subunit of rabbit hepatic lectin. Biochemistry 25, 6835-6841
60. Rice, K.G. and Lee, R.T. (1990) Modification of triantennary glycopeptide into probes for the asialoglycoprotein receptor of hepatocytes. J. Biol. Chem. 265, 18423-18428
61. Lee, K.B. and Lee, Y.C. (1994) Transfer of modified sialic acids by Trypanosoma cruzi trans-sialidase for attachment of functional groups to oligosaccharide. Anal. Biochem. 216, 358-364
62. Brossmer, R. and Gross, H.J. (1994) Sialic acid analogs and application for preparation of neoglycoproteins. Methods Enzymol. 247, 153-177
63. Brossmer, R. and Gross, H.J. (1994) Fluorescent and photoactivatable sialic acids. Methods Enzymol. 247, 177-193
64. Buckler, D.R., Haas, E., and Scheraga, H.A. (1993) C-Terminal labeling of ribonuclease A with an extrinsic fluorescent probe by carboxypeptidase Y-catalyzed transpeptidation in the presence of urea. Anal. Biochem. 209, 20-31
65. Novotny, M. V. and Sudor, J. (1993) High-performance capillary electrophoresis of glycoconjugates. Electrophoresis 14, 373-389
66. Yoon, J. and Czarnik, A.W. (1992) Fluorescent chemosensors of carbohydrates. A means of chemically communicating the binding of polyols in water based on chelation-enhanced quenching. J. Am. Chem. Soc. 114, 5874-5875