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Abstract:

It has been suggested that the FGF-2 binding site on heparan sulfate chains is a trisulfated pentasaccharide containing three hexuronic acid units. The configuration at C-5 of two of them being undetermined, we have synthesized the four possible pentasaccharides, and have evaluated their FGF-2 binding affinity through in vitro biological assays. The pentasaccharide containing L-iduronic acid as the sole hexuronic acid showed higher affinity for FGF-2 than the other pentasaccharides, where one hexuronic acid unit at least is D-glucuronic acid. Copyright (C) 1999.

Registro:

Documento: Artículo
Título:A synthetic heparan sulfate pentasaccharide, exclusively containing L-iduronic acid, displays higher affinity for FGF-2 than its D-glucuronic acid-containing isomers
Autor:Kovensky, J.; Duchaussoy, P.; Bono, F.; Salmivirta, M.; Sizun, P.; Herbert, J.-M.; Petitou, M.; Sinaÿ, P.
Filiación:Ecole Normale Supérieure, Département de Chimie, Associé au CNRS, 24 rue Lhomond, 75231 Paris Cedex 05, France
Sanofi Recherche, Haemobiology Research Department, 135 route d'Espagne, 31036 Toulouse Cedex, France
Uppsala University, Dept. Med. and Physiological Chem., Biomedical Center, PO Box 575, S-75123 Uppsala, Sweden
Sanofi Recherche, Exploratory Research Department, 371 rue du Professeur Joseph Blayac, 34184 Montpellier Cedex, France
Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Cd. Univ.-Pabellon II-3o, 1428 Buenos Aires, Argentina
Palabras clave:Carbohydrates; Glycosylation; Growth factors; Heparan sulfate; fibroblast growth factor 2; heparan sulfate; pentasaccharide; aorta; article; binding affinity; binding site; chemical structure; controlled study; human; human cell; intestine; synthesis; Aorta; Binding Sites; Carbohydrate Sequence; Cell Division; Cells, Cultured; Fibroblast Growth Factor 2; Glucuronic Acid; Heparitin Sulfate; Humans; Iduronic Acid; Isomerism; Molecular Sequence Data; Muscle, Smooth, Vascular; Oligosaccharides
Año:1999
Volumen:7
Número:8
Página de inicio:1567
Página de fin:1580
DOI: http://dx.doi.org/10.1016/S0968-0896(99)00106-6
Título revista:Bioorganic and Medicinal Chemistry
Título revista abreviado:Bioorg. Med. Chem.
ISSN:09680896
CODEN:BMECE
CAS:Fibroblast Growth Factor 2, 103107-01-3; Glucuronic Acid, 576-37-4; Heparitin Sulfate, 9050-30-0; Iduronic Acid, 3402-98-0; Oligosaccharides
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v7_n8_p1567_Kovensky

Referencias:

  • Yayon, A., Klagsbrun, M., Esko, J.D., Leder, P., Ornitz, D.M., (1991) Cell, 64, p. 841
  • Gallagher, J.T., (1994) Eur. J. Clin. Chem. Clin. Biochem., 32, p. 239
  • Moy, F.J., Sofran, M., Seddon, A., Kitchen, D., Böhlen, P., Aviezer, D., Yayon, A., Powers, R., (1997) Biochemistry, 63, p. 4782
  • Herr, A.B., Ornitz, D.M., Sasisekharan, R., Venkataraman, G., Waksman, G., (1997) J. Biol. Chem., 272, p. 16382
  • Turnbull, J.E., Fernig, D.E., Ke, Y., Wilkinson, M.C., Gallagher, J.T., (1992) J. Biol. Chem., 267, p. 10337
  • Guimond, S., Maccarana, M., Olwin, B.B., Lindahl, U., Rapraeger, A., (1993) J. Biol. Chem., 268, p. 23906
  • Walker, A., Turnbull, J.E., Gallagher, J.T., (1994) J. Biol. Chem., 269, p. 931
  • Ornitz, D.M., Herr, A.B., Nilsson, M., Westman, J., Svahn, C.-M., Waksman, G., (1995) Science, 268, p. 432
  • Maccarana, M., Casu, B., Lindahl, U., (1993) J. Biol. Chem., 268, p. 23898
  • Kovensky, J., Duchaussoy, P., Petitou, M., Sinaÿ, P., (1996) Tetrahedron: Asymmetry, 7, p. 3119
  • Tabeur, C., Machetto, F., Mallet, J.-M., Duchaussoy, P., Petitou, M., Sinaÿ, P., (1996) Carbohydr. Res., 281, p. 253
  • Pedretti, V., Mallet, J.-M., Sinaÿ, P., (1993) Carbohydr. Res., 244, p. 247
  • Veeneman, G.H., Van Leeuwen, S.H., Van Boom, J.H., (1990) Tetrahedron Lett., 31, p. 1331
  • Konradsson, P., Udodong, U.E., Fraser-Reid, B., (1990) Tetrahedron Lett., 31, p. 4313
  • Helferich, B., Portz, W., (1953) Chem. Ber., 86, p. 604
  • Sakai, K., Nakahara, Y., Ogawa, T., (1990) Tetrahedron Lett., 31, p. 3035
  • Koeners, H.J., Verhoeven, J., Van Boom, J.H., (1981) Tetrahedron Lett., 21, p. 381
  • Oltvoort, J.J., Van Boeckel, C.A.A., De Koning, J.H., Van Boom, J.H., (1981) Synthesis, p. 305
  • Petitou, M., Duchaussoy, P., Lederman, I., Choay, J., Sinaÿ, P., Jacquinet, J.-C., Torri, G., (1986) Carbohydr. Res., 147, p. 221
  • Fischer, B., Nudelman, A., Ruse, M., Herzig, J., Gottlieb, H.E., Keinan, E., (1984) J. Org. Chem., 49, p. 4988
  • Schmidt, R.R., Michel, J., (1984) Tetrahedron Lett., 25, p. 821
  • Schmidt, R.R., Michel, J., Roos, M., (1984) Liebigs. Ann. Chem., p. 1342
  • Ferro, D.R., Provasoli, A., Ragazzi, M., Torri, G., Casu, B., Gatti, G., Jacquinet, J.-C., Choay, J., (1986) J. Am. Chem. Soc., 108, p. 6773
  • Casu, B., Petitou, M., Provasoli, A., Sinaÿ, P., (1988) Trends Biochem. Sci., 13, p. 221
  • Kessler, H., Oschkinat, H., Griesinger, C., Bermel, W., (1986) J. Magn. Res., 70, p. 106
  • Kessler, P., NMR-Sim Version 2.6.1, , Bruker Analitik GmbH, Silberstreifen, D-76287 Rheinstetten, Germany
  • Ferro, D.R., Provasoli, A., Raggazzi, M., Casu, B., Torri, G., Bossennec, V., Perly, B., Choay, J., (1990) Carbohydr. Res., 195, p. 157
  • Jönsson, U., Fägerstam, L., Ivarsson, B., Johnsson, B., Karlsson, R., Lundh, K., Lofas, S., Ronnberg, I., (1991) Biotechniques, 11, p. 620
  • Mach, H., Volkin, D.B., Burke, C.J., Middaugh, C.R., Linhardt, R.J., Fromm, J.R., Loganathan, D., Mattson, L., (1993) Biochemistry, 32, p. 5480
  • Bono, F., Rigon, P., Lamarche, I., Savi, P., Salel, V., Herbert, J.-M., (1997) Biochem. J., 326, p. 661
  • Faham, S., Hileman, R.E., Fromm, J.R., Linhardt, R.J., Rees, D.C., (1996) Science, 271, p. 1116

Citas:

---------- APA ----------
Kovensky, J., Duchaussoy, P., Bono, F., Salmivirta, M., Sizun, P., Herbert, J.-M., Petitou, M.,..., Sinaÿ, P. (1999) . A synthetic heparan sulfate pentasaccharide, exclusively containing L-iduronic acid, displays higher affinity for FGF-2 than its D-glucuronic acid-containing isomers. Bioorganic and Medicinal Chemistry, 7(8), 1567-1580.
http://dx.doi.org/10.1016/S0968-0896(99)00106-6
---------- CHICAGO ----------
Kovensky, J., Duchaussoy, P., Bono, F., Salmivirta, M., Sizun, P., Herbert, J.-M., et al. "A synthetic heparan sulfate pentasaccharide, exclusively containing L-iduronic acid, displays higher affinity for FGF-2 than its D-glucuronic acid-containing isomers" . Bioorganic and Medicinal Chemistry 7, no. 8 (1999) : 1567-1580.
http://dx.doi.org/10.1016/S0968-0896(99)00106-6
---------- MLA ----------
Kovensky, J., Duchaussoy, P., Bono, F., Salmivirta, M., Sizun, P., Herbert, J.-M., et al. "A synthetic heparan sulfate pentasaccharide, exclusively containing L-iduronic acid, displays higher affinity for FGF-2 than its D-glucuronic acid-containing isomers" . Bioorganic and Medicinal Chemistry, vol. 7, no. 8, 1999, pp. 1567-1580.
http://dx.doi.org/10.1016/S0968-0896(99)00106-6
---------- VANCOUVER ----------
Kovensky, J., Duchaussoy, P., Bono, F., Salmivirta, M., Sizun, P., Herbert, J.-M., et al. A synthetic heparan sulfate pentasaccharide, exclusively containing L-iduronic acid, displays higher affinity for FGF-2 than its D-glucuronic acid-containing isomers. Bioorg. Med. Chem. 1999;7(8):1567-1580.
http://dx.doi.org/10.1016/S0968-0896(99)00106-6