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Volumn 21, Issue 5, 2004, Pages 179-195

Synthesis of heparin-like oligosaccharides on polymer supports

Author keywords

carbohydrates; heparin; oligosaccharides; solid phase synthesis; synthesis design

Indexed keywords

CARBOHYDRATE DERIVATIVE; CARBOXYL GROUP; DISACCHARIDE; ESTER; GLYCOSAMINOGLYCAN; HEPARIN DERIVATIVE; HEXASACCHARIDE; MACROGOL; OCTASACCHARIDE; OLIGOSACCHARIDE; POLYMER; POLYSTYRENE; RESIN; SUCCINIC ACID; TRICHLOROACETIMIDIC ACID; UNCLASSIFIED DRUG; URONIC ACID;

EID: 6344258876     PISSN: 02820080     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:GLYC.0000045091.18392.a8     Document Type: Article
Times cited : (47)

References (37)
  • 3
    • 0035707396 scopus 로고    scopus 로고
    • Structure and biological interactions of heparin and heparan sulfate
    • Casu B, Lindahl U, Structure and biological interactions of heparin and heparan sulfate, Adv Carbohydr Chem Biochem 57, 159-206 (2001).
    • (2001) Adv Carbohydr Chem Biochem , vol.57 , pp. 159-206
    • Casu, B.1    Lindahl, U.2
  • 5
    • 0020108082 scopus 로고
    • Further characterization of the antithrombin-binding sequence in heparin
    • Thunberg L, Bäckström G, Lindahl U, Further characterization of the antithrombin-binding sequence in heparin, Carbohydr Res 100, 393-410 (1982).
    • (1982) Carbohydr Res , vol.100 , pp. 393-410
    • Thunberg, L.1    Bäckström, G.2    Lindahl, U.3
  • 6
    • 0031733974 scopus 로고    scopus 로고
    • Diversity does make a difference: Fibroblast growth factor-heparin interactions
    • Faham S, Linhardt RJ, Rees DC, Diversity does make a difference: Fibroblast growth factor-heparin interactions, Curr Opin Struct Biol 8, 578-86 (1998).
    • (1998) Curr Opin Struct Biol , vol.8 , pp. 578-586
    • Faham, S.1    Linhardt, R.J.2    Rees, D.C.3
  • 7
    • 0035903106 scopus 로고    scopus 로고
    • Sequence analysis of heparan sulfate epitopes with graded affinities for fibroblast growth factors 1 and 2
    • Kreuger J, Salmivirta M, Sturiale L, Giménez-Gallego G, Lindhal U, Sequence analysis of heparan sulfate epitopes with graded affinities for fibroblast growth factors 1 and 2, J Biol Chem 276, 30744-52 (2001).
    • (2001) J Biol Chem , vol.276 , pp. 30744-30752
    • Kreuger, J.1    Salmivirta, M.2    Sturiale, L.3    Giménez-Gallego, G.4    Lindhal, U.5
  • 8
    • 0029866647 scopus 로고    scopus 로고
    • Heparin structure and interactions with basic fibroblast growth factor
    • Faham S, Hileman SE, Fromm JR, Lindhardt RJ, Rees DC, Heparin structure and interactions with basic fibroblast growth factor, Science 271, 1116-20 (1996).
    • (1996) Science , vol.271 , pp. 1116-1120
    • Faham, S.1    Hileman, S.E.2    Fromm, J.R.3    Lindhardt, R.J.4    Rees, D.C.5
  • 11
    • 0034718796 scopus 로고    scopus 로고
    • Crystal structure of fibroblast growth factor receptor ectodomain bound to ligand and heparin
    • Pellegrini L, Burke DF, Von Delft F, Mulloy B, Blundell TL, Crystal structure of fibroblast growth factor receptor ectodomain bound to ligand and heparin, Nature 407, 1029-34 (2000).
    • (2000) Nature , vol.407 , pp. 1029-1034
    • Pellegrini, L.1    Burke, D.F.2    Von Delft, F.3    Mulloy, B.4    Blundell, T.L.5
  • 13
    • 0036434884 scopus 로고    scopus 로고
    • The activation of fibroblast growth factors by heparin: Synthesis and structural study of rationally modified heparin-like oligosaccharides
    • Ojeda R, Angulo J, Nieto PM, Martin-Lomas M, The activation of fibroblast growth factors by heparin: Synthesis and structural study of rationally modified heparin-like oligosaccharides, Can J Chem 80, 673-85 (2002).
    • (2002) Can J Chem , vol.80 , pp. 673-685
    • Ojeda, R.1    Angulo, J.2    Nieto, P.M.3    Martin-Lomas, M.4
  • 14
    • 0042202626 scopus 로고    scopus 로고
    • Synthesis and structural study of two new heparin-like hexasaccharides
    • Lucas R, Angulo J, Nieto PM, Martin-Lomas M, Synthesis and structural study of two new heparin-like hexasaccharides, Org Biomol Chem 1, 2253-66 (2003).
    • (2003) Org Biomol Chem , vol.1 , pp. 2253-2266
    • Lucas, R.1    Angulo, J.2    Nieto, P.M.3    Martin-Lomas, M.4
  • 15
    • 0042786019 scopus 로고    scopus 로고
    • Some key experimental features of a modular synthesis of heparin-like oligosaccharides
    • de Paz JL, Ojeda R, Reichardt N, Martin-Lomas M, Some key experimental features of a modular synthesis of heparin-like oligosaccharides, Eur J Org Chem 3308-24 (2003).
    • (2003) Eur J Org Chem , pp. 3308-3324
    • De Paz, J.L.1    Ojeda, R.2    Reichardt, N.3    Martin-Lomas, M.4
  • 16
    • 0037804580 scopus 로고    scopus 로고
    • A molecular dynamics description of the conformational flexibility of the L-iduronate ring in glycosaminoglycans
    • Angulo J, Nieto PM, Martin-Lomas M, A molecular dynamics description of the conformational flexibility of the L-iduronate ring in glycosaminoglycans, Chem Commun 2486-7 (2003).
    • (2003) Chem Commun , pp. 2486-2487
    • Angulo, J.1    Nieto, P.M.2    Martin-Lomas, M.3
  • 18
    • 0034498920 scopus 로고    scopus 로고
    • Solid-Phase oligosaccharides synthesis and combinatorial carbohydrate libraries
    • Seeberger PH, Haase WC, Solid-Phase oligosaccharides synthesis and combinatorial carbohydrate libraries, Chem Rev 100, 4349-93 (2000).
    • (2000) Chem Rev , vol.100 , pp. 4349-4393
    • Seeberger, P.H.1    Haase, W.C.2
  • 19
    • 0035936861 scopus 로고    scopus 로고
    • Automated solid-phase synthesis of oligosaccharides
    • Plante OJ, Palmacci ER, Seeberger PH, Automated solid-phase synthesis of oligosaccharides, Science 291, 1523-7 (2001).
    • (2001) Science , vol.291 , pp. 1523-1527
    • Plante, O.J.1    Palmacci, E.R.2    Seeberger, P.H.3
  • 20
    • 0036180240 scopus 로고    scopus 로고
    • Oligosaccharide synthesis in solution and on solid support with glycosyl phosphates
    • Palmacci ER, Plante OJ, Seeberger PH, Oligosaccharide synthesis in solution and on solid support with glycosyl phosphates, Eur J Org Chem 595-606 (2002).
    • (2002) Eur J Org Chem , pp. 595-606
    • Palmacci, E.R.1    Plante, O.J.2    Seeberger, P.H.3
  • 21
    • 0033529691 scopus 로고    scopus 로고
    • Synthesis of disaccharidic sub-units of a new series of heparin related oligosaccharides
    • La Ferla B, Lay L, Guerrini M, Poletti L, Panza L, Russo G, Synthesis of disaccharidic sub-units of a new series of heparin related oligosaccharides, Tetrahedron 55, 9867-80 (1999).
    • (1999) Tetrahedron , vol.55 , pp. 9867-9880
    • La Ferla, B.1    Lay, L.2    Guerrini, M.3    Poletti, L.4    Panza, L.5    Russo, G.6
  • 22
    • 0034994242 scopus 로고    scopus 로고
    • Towards a modular approach for heparin synthesis
    • Haller M, Boons GJ, Towards a modular approach for heparin synthesis, J Chem Soc Perkin Trans 1, 814-22 (2001).
    • (2001) J Chem Soc Perkin Trans , vol.1 , pp. 814-822
    • Haller, M.1    Boons, G.J.2
  • 23
    • 0036314235 scopus 로고    scopus 로고
    • Selectively protected disaccharide building blocks for modular synthesis of heparin fragments
    • Haller M, Boons GJ, Selectively protected disaccharide building blocks for modular synthesis of heparin fragments, Eur J Org Chem 2033-8 (2002).
    • (2002) Eur J Org Chem , pp. 2033-2038
    • Haller, M.1    Boons, G.J.2
  • 25
    • 0142106325 scopus 로고    scopus 로고
    • Synthesis of heparin-like oligosaccharides on a soluble polymer support
    • Ojeda R, de Paz JL, Martin-Lomas M, Synthesis of heparin-like oligosaccharides on a soluble polymer support, Chem Commun 2486-7 (2003).
    • (2003) Chem Commun , pp. 2486-2487
    • Ojeda, R.1    De Paz, J.L.2    Martin-Lomas, M.3
  • 26
    • 0035590822 scopus 로고    scopus 로고
    • Recent advances in the synthetic studies of glycosaminoglycans
    • For a reviews see Tamura J, Recent advances in the synthetic studies of glycosaminoglycans, Trend Glycosci Glycotechnol 13, 65-88 (2001).
    • (2001) Trend Glycosci Glycotechnol , vol.13 , pp. 65-88
    • Tamura, J.1
  • 27
    • 33748233635 scopus 로고
    • The unique antithrombin III binding domain of heparin: A lead to new synthetic antithrombotics
    • For a review see van Boeckel CAA, Petitou M, The unique antithrombin III binding domain of heparin: A lead to new synthetic antithrombotics, Angew Chem Int Ed 32, 1671-90 (1993).
    • (1993) Angew Chem Int Ed , vol.32 , pp. 1671-1690
    • Van Boeckel, C.A.A.1    Petitou, M.2
  • 29
    • 0028186224 scopus 로고
    • Kinzy, Anomeric-oxygen activation for glycoside synthesis: The trichloroacetimidate method
    • Schmidt RR, Kinzy, Anomeric-oxygen activation for glycoside synthesis: The trichloroacetimidate method, Adv Carbohydr Chem Biochem 50, 21-123 (1994).
    • (1994) Adv Carbohydr Chem Biochem , vol.50 , pp. 21-123
    • Schmidt, R.R.1
  • 30
    • 49549143786 scopus 로고
    • Selective cleavage of anomeric acetyl groups of acetylated glycosyl residues by hydrazine
    • Excoffier G, Gagnaire D, Utille JP, Selective cleavage of anomeric acetyl groups of acetylated glycosyl residues by hydrazine, Carbohydr Res 39, 368-73 (1975).
    • (1975) Carbohydr Res , vol.39 , pp. 368-373
    • Excoffier, G.1    Gagnaire, D.2    Utille, J.P.3
  • 31
    • 0001686537 scopus 로고
    • Polymer-supported solution synthesis of oligosaccharides
    • Douglas SP, Whitfield DM, Krepinsky JJ, Polymer-supported solution synthesis of oligosaccharides, J Am Chem Soc 113, 5095-7 (1991).
    • (1991) J Am Chem Soc , vol.113 , pp. 5095-5097
    • Douglas, S.P.1    Whitfield, D.M.2    Krepinsky, J.J.3
  • 32
    • 0001408315 scopus 로고
    • Synthesis of heparan fragments-a chemical synthesis of the trisaccharide O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-alpha-D-glucopyranosyl)-(1 → 4)-O-(2-O-sulfo-alpha-L-idopyranosyluronic acid)-(1 → 4)-2-deoxy-2- sulfamido-6-O-sulfo-D-glucopyranose heptasodium salt
    • Jaquinet JC, Petitou M, Duchaussoy R Lederman I, Choay J, Torri G, Sinaÿ P, Synthesis of heparan fragments-a chemical synthesis of the trisaccharide O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-alpha-D-glucopyranosyl)-(1 → 4)-O-(2-O-sulfo-alpha-L-idopyranosyluronic acid)-(1 → 4)-2-deoxy-2-sulfamido-6-O-sulfo-D-glucopyranose heptasodium salt, Carbohydr Res 130, 221-41 (1984).
    • (1984) Carbohydr Res , vol.130 , pp. 221-241
    • Jaquinet, J.C.1    Petitou, M.2    Duchaussoy, R.3    Lederman, I.4    Choay, J.5    Torri, G.6    Sinaÿ, P.7
  • 33
    • 0032769229 scopus 로고    scopus 로고
    • A new route to L-iduronate building-blocks for the synthesis of heparin-like oligosaccharides
    • Ojeda R, de Paz JL, Martin-Lomas H, Lassaletta JM, A new route to L-iduronate building-blocks for the synthesis of heparin-like oligosaccharides, Synlett, 1316-8 (1999).
    • (1999) Synlett , pp. 1316-1318
    • Ojeda, R.1    De Paz, J.L.2    Martin-Lomas, H.3    Lassaletta, J.M.4
  • 35
    • 0035477628 scopus 로고    scopus 로고
    • A mild and effective method for the transesterification of carboxylic acid esters
    • Baumhof P, Mazitschek R, Giannis A, A mild and effective method for the transesterification of carboxylic acid esters, Angew Chem Int Ed 40, 3672-4 (2001).
    • (2001) Angew Chem Int Ed , vol.40 , pp. 3672-3674
    • Baumhof, P.1    Mazitschek, R.2    Giannis, A.3
  • 36
    • 0035905427 scopus 로고    scopus 로고
    • Solid-phase capture-release strategy applied to oligosaccharide synthesis on a soluble polymer support
    • Ando H, Manabe S, Nakahara Y, Ito Y, Solid-phase capture-release strategy applied to oligosaccharide synthesis on a soluble polymer support, Angew Chem Int Ed 40, 4725-8 (2001).
    • (2001) Angew Chem Int Ed , vol.40 , pp. 4725-4728
    • Ando, H.1    Manabe, S.2    Nakahara, Y.3    Ito, Y.4
  • 37
    • 0034671385 scopus 로고    scopus 로고
    • The "resin-capture-release" hybrid technique: A merger between solid- and solution-phase synthesis
    • A. Kirshing, H. Monenschain, R. Wittenberg, The "resin-capture- release" hybrid technique: a merger between solid- and solution-phase synthesis, Chem Eur J 6, 4445-50, (2000).
    • (2000) Chem Eur J , vol.6 , pp. 4445-4450
    • Kirshing, A.1    Monenschain, H.2    Wittenberg, R.3


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