Carbohydrate ligands of human C-reactive protein: Binding of neoglycoproteins containing galactose-6-phosphate and galactose-terminated disaccharide

Glycoconjugate Journal

Volumn 23, Issue 5-6, 2006, Pages 317-327

  Lee, Reiko T ^a   Lee, Yuan C ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

C reactive protein; Europium fluorescence; Ligand binding assay; Neoglycoproteins

Indexed keywords

ALDEHYDE; BOVINE SERUM ALBUMIN; C REACTIVE PROTEIN; CALCIUM ION; CARBOHYDRATE; DISACCHARIDE; GALACTOSE; GALACTOSE 6 PHOSPHATE; GALACTOSE PHOSPHATE; GLYCOSIDE; LIGAND; N ACETYLGALACTOSAMINE; NEOGLYCOPROTEIN; PHOSPHATE; PHOSPHORYLCHOLINE; SUGAR; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; BINDING AFFINITY; BINDING SITE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CONTROLLED STUDY; CULTURE MEDIUM; HUMAN; LIGAND BINDING; PH; PRIORITY JOURNAL; PROTEIN CARBOHYDRATE INTERACTION; PROTEIN CONFORMATION; PROTEIN STRUCTURE; STRUCTURE ANALYSIS; X RAY ANALYSIS;

BINDING SITES; BINDING, COMPETITIVE; C-REACTIVE PROTEIN; DISACCHARIDES; GALACTOSE; GALACTOSEPHOSPHATES; GLYCOPROTEINS; HUMANS; LIGANDS;

BOS TAURUS;

EID: 33746881469     PISSN: 02820080     EISSN: 15734986     Source Type: Journal    
DOI: 10.1007/s10719-006-6173-x     Document Type: Article

References (37)

1. Volanakis, J.E.: Human C-reactive protein: expression, structure, and function. Mol. Immunol. 38, 189-97 (2001)
2. Gershov, D., Kim, S., Brot, N., Elkon, K.B.: C-reactive protein binds to apoptotic cells, protects the cells from assembly of the terminal complement components, and sustains an antiinflammatory innate immune response: implications for systimic autoimmunity. J. Exp. Med. 192, 1353-63 (2000)
3. Szalai, A.J.: The antimicrobial activity of C-reactive protein. Microbes Infect. 4, 201-5 (2002)
4. Gotschlich, E.C., Liu, T.Y.: Structural and immunological studies on the pneumococcal C polysaccharide. J. Biol. Chem. 242, 463-70 (1967)
5. Higginbotham, J.D., Heidelberger, M., Gotschlich, E.C.: Degradation of a pneumococcal type-specific polysaccharide with exposure of group-specificity. Proc Natl Acad Sci USA 67, 138-42 (1970)
6. Gotschlich, E.C., Liu, T.Y., Oliveira, E.B.: Binding of C-reactive protein to C-carbohydrate and PC-substituted protein. Ann. NY Acad. Sci. 389, 163-71 (1982)
7. Potempa, L.A., Siegel, J.N., Gewurz, H.: Binding reactivity of C-reactive protein for polycations. II. Modulatory effects of calcium and phosphocholine. J. Immunol. 127, 1509-14 (1981)
8. Shrive, A.K., Cheetham, G.M., Holden, D., Myles, D.A., Turnell, W.G., Volanakis, J.E., Pepys, M.B., Bloomer, A.C., Greenhough, T.J.: Three dimensional structure of human C-reactive protein. Nat. Struct. Biol. 3, 346-54 (1996)
9. Thompson, D., Pepys, M.B., Wood, S.P.: The physiological structure of human C-reactive protein and its complex with phosphocholine. Structure Fold Des. 7, 169-77 (1999)
10. Potempa, L.A., Siegel, J.N., Fiedel, B.A., Potempa, R.T., Gewurz, H.: Expression, detection and assay of a neoantigen (Neo-CRP) associated with a free, human C-reactive protein subunit. Mol. Immunol. 24, 531-41 (1987)
11. Ying, S.C., Gewurz, H., Kinoshita, C.M., Potempa, L.A., Siegel, J.N.: Identification and partial characterization of multiple native and neoantigenic epitopes of human C-reactive protein by using monoclonal antibodies. J. Immunol. 143, 221-8 (1989)
12. Potempa, L.A., Zeller, J.M., Fiedel, B.A., Kinoshita, C.M., Gewurz, H.: Stimulation of human neutrophils, monocytes, and platelets by modified C-reactive protein (CRP) expressing a neoantigenic specificity. Inflammation 12, 391-405 (1988)
13. Rees, R.F., Gewurz, H., Siegel, J.N., Coon, J., Potempa, L.A.: Expression of a C-reactive protein neoantigen (neo-CRP) in inflamed rabbit liver and muscle. Clin. Immunol. Immunopathol. 48, 95-107 (1988)
14. Diehl, E.E., Haines, G.K., 3rd, Radosevich, J.A., Potempa, L.A.: Immunohistochemical localization of modified C-reactive protein antigen in normal vascular tissue. Am. J. Med. Sci. 319, 79-83 (2000)
15. Szalai, A.J., Agrawal, A., Greenhough, T.J., Volanakis, J.E.: C-reactive protein: structural biology, gene expression, and host defense function. Immunol. Res. 16, 127-36 (1997)
16. Lee, R.T., Takagahara, I., Lee, Y.C.: Mapping the binding areas of human C-reactive protein for phophorylcholine and polycationic compounds. Relationship between the two types of binding sites. J. Biol. Chem. 277, 225-32 (2002)
17. Kottgen, E., Hell, B., Kage, A., Tauber, R.: Lectin specificity and binding characteristics of human C-reactive protein. J. Immunol. 149, 445-53 (1992)
18. Lee, R.T., Lee, Y.C.: Carbohydrate-binding properties of human neo-CRP and its relationship to phosphorylcholine-binding site. Glycobiology 13, 11-21 (2003)
19. Weigel, P.H., Naoi, M., Roseman, S., Lee, Y.C.: Preparation of 6-aminohexyl D-aldopyranosides. Carbohydr. Res. 70, 83-91 (1979)
20. Stults, N., Lee, Y.C., Hoppe, C.A., Kawaguchi, K., Kohda, S., Takagahara, I., Koishi, T., Liu, T.Y.: Preparation of phosphorylcholine derivatives of bovine serum albumin and their application to the affinity chromatography of C-reactive protein. Anal. Biochem. 161, 567-73 (1987)
21. Lee, R.T., Lee, Y.C.: Preparation and some biochemical properties of neoglycoproteins produced by reductive amination of thioglycosides contianing an ω -aldehydoaglycon. Biochemistry 19, 156-63 (1980)
22. McKelvy, J.F., Lee, Y.C.: Microheterogeneity of the carbohydrate group of Aspergillus oryzae α-amylase. Arch. Biochem. Biophys. 132, 99-110 (1969)
23. Ames, B.N., Dubin, D.T.: The role of polyamines in the neutralization of bacteriophage deoxyribonucleic acid. J. Biol. Chem. 235, 769-75 (1960)
24. Smith, P.K., Krohn, R.I., Hermanson, G.T., Mallia, A.K., Gartner, F.H., Provenzano, M.D., Fujimoto, E.K., Goeke, N.M., Olson, B.J., Klenk, D.C.: Measurement of protein using bicinchoninic acid. Anal. Biochem. 150, 76-85 (1985)
25. Naoi, M., Lee, Y.C.: A fluorometric measurement of ligands incorporated into BrCN-activated polysaccharides. Anal. Biochem. 57, 640-4 (1974)
26. Hemmila, I.A., Dakubu, S., Mukkala, V.-M., Siitarl, H., Lovgren, T.: Europium as a label in time-resolved immunofluorometric assays. Anal. Biochem. 137, 335-43 (1984)
27. Brown, C.A., Brown, H.C.: Catalytic hydrogenation II. A new, convenient technique for laboratory hydrogenations. A simple, automatic device for atmospheric pressure hydrogenations. J. Org. Chem. 31, 3989-95 (1966)
28. Yu, K.-L., Fraser-Reid, B.:Anovel reagent for the synthesis of myoinositol phosphates: N, N-diisopropyl dibenzyl phosphoramidite. Tetrahedron Letts. 29, 979-82 (1988)
29. Tegge, W., Ballou, C.E.: Chiral syntheses of D- and L-myoinositol 1,4,5-triphosphate. Proc. Natl. Acad. Sci. USA 86, 94-8 (1989)
30. Lee, R.T., Wong, T.C., Lee, Y.C.: Synthesis of 6′-aminohexyl 2-acetamido-2-deoxy-D-galactoside isomers and a unique isomerization catalyzed by ion exchange resin. J. Carbohydr. Chem. 5, 343-57 (1986)
31. Lee, R.T., Lee, Y.C.: A derivative of diethylentriaminepentaacetic acid for europium labeling of proteins. Bioconjugate J. 12, 845-9 (2001)
32. Butler, J.E.: Solid phases in immunoassay. In Immunoassay, vol., edited by Christopoulos TK (Academic Press, San Diego, 1996), pp. 205-25.
33. Lee, R.T., Shinohara, Y., Hasegawa, Y., Lee, Y.C.: Lectin-carbohydrate Interactions: Fine specificity difference between two mannose-binding proteins. Bioscience Reports 19, 283-92 (1999)
34. Lee, R.T., Ichikawa, Y., Fay, M., Drickamer, K., Shao, M.C., Lee, Y.C.: Ligand-binding characteristics of rat serum-type mannose-binding protein (MBP-A). J. Biol. Chem. 266, 4810-5 (1991)
35. Ng, K.K.-S., Drickamer, K., Weis, W.I.: Structural analysis of monosaccharide recognition by rat liver mannose-binding protein. J. Biol. Chem. 271, 663-74 (1996)
36. Culley, F.J., Bodman-Smith, K.B., Ferguson, M.A., Nikolaev, A.V., Shantilal, N., Raynes, J.G.: C-reactive protein binds to phosphorylated carbohydrates. Glycobiology 10, 59-65 (2000)
37. Jennings, H.J., Lugowski, C., Young, N.M.: Structure of the complex polysaccharides C-substance from Streptococcus pneumoniae type 1. Biochemistry 19, 4712-9 (1980)