A novel strategy to generate biologically active neo-glycosaminoglycan conjugates

Glycobiology

Volumn 9, Issue 12, 1999, Pages 1331-1336

  Rong, Jianhui ^a   Nordling, Kerstin ^b   Björk, Ingemar ^b   Lindahl, Ulf ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b SWEDISH UNIVERSITY OF AGRICULTURAL SCIENCES   (Sweden)

Author keywords

Antithrombin; Heparin; Neo glycosaminoglycan; Thrombin

Indexed keywords

ANTICOAGULANT AGENT; ANTITHROMBIN; CARBOHYDRATE; DISACCHARIDE; GLYCOSAMINOGLYCAN; HEPARAN SULFATE; HEPARIN; NITROUS ACID; POLYSACCHARIDE;

ANTICOAGULATION; ARTICLE; COMPLEX FORMATION; CONJUGATE; CONTROLLED STUDY; DEAMINATION; DRUG CONJUGATION; GEL CHROMATOGRAPHY; GLYCOSAMINOGLYCAN METABOLISM; HUMAN; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0033456287     PISSN: 09596658     EISSN: None     Source Type: Journal    
DOI: 10.1093/glycob/9.12.1331     Document Type: Article

References (30)

1. Barzu, T., Level, M., Petitou, M., Lormeau, J.C., Choay, J., Schols, D., Baba, M., Pauwels, R., Witvrouw, M. and De Clercq, E. (1993) Preparation and anti-HIV activity of O-acylated heparin and dermatan sulfate derivatives with low anticoagulant effect. J. Med. Chem., 36, 3546-3555.
2. Bitter, T. and Muir, H.M. (1962) A modified uronic acid carbazole reaction. Anal. Biochem., 4, 330-333.
3. Bourin, M.C. and Lindahl, U. (1993) Glycosaminoglycans and the regulation of blood coagulation. Biochem. J., 289, 313-330.
4. Conrad, H.E. (1998) Heparin-Binding Proteins. San Diego, Academic Press.
5. Doi, E., Shibata, D. and Motoba, T. (1981) Modified colorimetric ninhydrin methods for peptide assay. Anal. Biochem., 118, 173-184.
6. Ellman, G.E. (1959) Tissue sulfhydryl groups. Arch. Biochem. Biophys., 82, 70-77.
7. Ersdal, B.E., Lu, A., Peng, X., Picard, V., Zendehrouh, P., Turk, B. and Bjork, I., Olson, S. T; and Bock, S. C; (1995) Elimination of glycosylation heterogeneity affecting heparin affinity of recombinant human antithrombin III by expression of a beta-like variant in baculovirus-infected insect cells. Biochem. J., 310, 323-330.
8. Grootenhuis, P.D., Westerduin, P., Meuleman, D., Petitou, M. and van-Boeckel, C.A. (1995) Rational design of synthetic heparin analogues with tailor-made coagulation factor inhibitory activity. Nat. Struct. Biol., 2, 736-739.
9. Guimond, S., Maccarana, M., Olwin, B.B., Lindahl, U. and Rapraeger, A.C. (1993) Activating and inhibitory heparin sequences for FGF-2 (basic FGF). Distinct requirements for FGF-1, FGF-2 and FGF-4. J. Biol. Chem., 268, 23906-23914.
10. Hoffman, J., Larm, O. and Scholander, E. (1983) A new method for covalent coupling of heparin and other glycosaminoglycans to substances containing primary amino groups. Carbohydr. Res., 117, 328.
11. Höök, M., Björk, I., Hopwood, J. and Lindahl, U. (1976) Anticoagulant activity of heparin: separation of high-activity and low-activity heparin species by affinity chromatography on immobilized antithrombin. FEBS Lett., 66, 90-93.
12. Lindahl, U., Cifonelli, J.A., Lindahl, B. and Rodén, L. (1965) The role of serine in the linkage of heparin to protein. J. Biol. Chem., 240, 2817-2820.
13. Linhardt, R.J., Turnbull, J.E., Wang, H.M., Loganathan, D. and Gallagher, J.T. (1990) Examination of the substrate specificity of heparin and heparan sulfate lyases. Biochemistry, 29, 2611-2617.
14. Lortat-Jacob, H., Turnbull, J.E. and Grimaud, J.A. (1995) Molecular organization of the interferon gamma-binding domain in heparan sulphate. Biochem. J., 310, 497-505.
15. Ludwigs, U., Elgavish, A., Esko, J.D., Meezan, E. and Rodén, L. (1987) Reaction of unsaturated uronic acid residues with mercuric salts. Cleavage of the hyaluronic acid disaccharide 2-acetamido-2-deoxy-3-O-(β-D-gluco-4-enepyranosyluronic acid)-D-glucose. Biochem. J., 245, 795-804.
16. Lyon, M., Rushton, G. and Gallagher, J.T. (1997) The interaction of the transforming growth factor-betas with heparin/heparan sulfate is isoform-specific. J. Biol. Chem., 272, 18000-18006.
17. Möller, H.J., Heinegard, D. and Poulsen, J.H. (1993) Combined alcian blue and silver staining of subnanogram quantities of proteoglycans and glycosaminoglycans in sodium dodecyl sulfate-polyacrylamide gels. Anal. Biochem., 209, 169-175.
18. Olson, S.T., Björk, I. and Shore, J.D. (1993) Kinetic characterization of heparin-catalyzed and uncatalyzed inhibition of blood coagulation proteinases by antithrombin. Methods Enzymol., 222, 525-559.
19. Oscarsson, L.G., Pejler, G. and Lindahl, U. (1989) Location of the antithrombin-binding sequence in the heparin chain. J. Biol. Chem., 264, 296-304.
20. Pejler, G., Lindahl, U., Larm, O., Scholander, E., Sandgren, E. and Lundblad, A. (1988) Monoclonal antibodies specific for oligosaccharides prepared by partial nitrous acid deamination of heparin. J. Biol. Chem., 263, 5197-5201.
21. Petitou, M. (1992) Chemical synthesis and hemisynthesis in the field of glycosaminoglycans. Adv. Exp. Med. Biol., 313, 21-30.
22. Petitou, M., Coudert, C., Level, M., Lormeau, J.C., Zuber, M., Simenel, C., Fournier, J.P. and Choay, J. (1992) Selectively O-acetylated glycosaminoglycan derivatives. Carbohydr. Res., 236, 107-119.
23. Salmivirta, M., Lidholt, K. and Lindahl, U. (1996) Heparan sulfate: a piece of information. FASEB J., 10, 1270-79.
24. Shively, J.E. and Conrad, H.E. (1976) Formation of anhydrosugars in the chemical depolymerization of heparin. Biochemistry, 15, 3932-3942.
25. Spillmann, D., Witt, D. and Lindahl, U. (1998) Defining the interleukin-8-binding domain of heparan sulfate. J. Biol. Chem., 273, 15487-15493.
26. Spivak-Kroizman, T., Lemmon, M.A., Dikic, I., Ladbury, J.E., Pinchasi, D., Huang, J., Jaye, M., Crumley, G., Schlessinger, J. and Lax, I. (1994) Heparin-induced oligomerization of FGF molecules is responsible for FGF receptor dimerization, activation and cell proliferation. Cell, 79, 1015-1024.
27. Stringer, S.E. and Gallagher, J.T. (1997) Specific binding of the chemokine platelet factor 4 to heparan sulfate. J. Biol. Chem., 272, 20508-20514.
28. Turk, B., Brieditis, I., Bock, S.C., Olson, S.T. and Björk, I. (1997) The oligosaccharide side chain on Asn-135 of α-antithrombin, absent in β-antithrombin, decreases the heparin affinity of the inhibitor by affecting the heparin-induced conformational change. Biochemistry, 36, 6682-6691.
29. van Boeckel, C.A., Grootenhuis, P.D. and Visser, A. (1994) A mechanism for heparin-induced potentiation of antithrombin III. Nat. Struct. Biol., 1, 423-425.
30. Walker, A., Turnbull, J.E. and Gallagher, J.T. (1994) Specific heparan sulfate saccharides mediate the activity of basic fibroblast growth factor. J. Biol. Chem., 269, 931-935.