Studies on selectin blockers. 6. Discovery of homologous fucose sugar unit necessary for E-selectin binding

Journal of Medicinal Chemistry

Volumn 41, Issue 13, 1998, Pages 2302-2307

  Hiramatsu, Yasuyuki ^a   Moriyama, Hideki ^a   Kiyoi, Takao ^a   Tsukida, Takahiro ^a   Inoue, Yoshimasa ^a   Kondo, Hirosato ^a  

^a KANEBO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIPEPTIDE; ENDOTHELIAL LEUKOCYTE ADHESION MOLECULE 1; FUCOSE; SELECTIN;

ARTICLE; CALCIUM BINDING; CARBOHYDRATE ANALYSIS; DRUG CONFORMATION; DRUG DESIGN; DRUG SYNTHESIS; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; STRUCTURE ACTIVITY RELATION;

CARBOHYDRATE SEQUENCE; DIPEPTIDES; DRUG DESIGN; E-SELECTIN; FUCOSE; GLYCOSIDES; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR MIMICRY; MOLECULAR SEQUENCE DATA; PROTEIN BINDING; PROTEIN CONFORMATION;

EID: 0032543615     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9707481     Document Type: Article

References (39)

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13. For recent examples of elegant strategies for oligosaccharide synthesis, see: (a) Kondo, H.; Ichikawa, Y.; Wong, C.-H. β-Sialyl Phosphite and Phosphoramidite: Synthesis and Application to the Chemoenzymatic Synthesis of CMP-Sialic Acid and Sialyl Oligosaccharides. J. Am. Chem. Soc. 1992, 114, 8748-8750. (b) Halcomb, R. L.; Huang, H.; Wong, C.-H. Solution- and Solid-Phase Synthesis of Inhibitors of H. Pylori Attachment and E-Selectin-Mediated Leukocyte Adhesion. J. Am. Chem. Soc. 1994, 116, 11315-11322. (c) Mehta, S.; Pinto, B. M. Novel Glycosidation Methodology; The Use of Phenyl Selenoglycosides as Glycosyl Donors and Acceptors in Oligosaccharide Synthesis. J. Org. Chem. 1993, 58, 3269-3276. (d) Raghavan, S.; Kahne, D. A One-Step Synthesis of the Ciclamycin Trisaccharide. J. Am. Chem. Soc. 1993, 115, 1580-1581. (e) Yamada, H.; Harada, T.; Takahashi, T. Synthesis of an Elicitor-Active Hexaglucoside Analogue by a One-Pot, Two-Step Glycosidation Procedure. J. Am. Chem. Soc. 1994, 116, 7919-7920. (f) Kanie, O.; Ito, Y.; Ogawa, T. Orthogonal Glycosylation Strategy in Oligosaccharide Synthesis. J. Am. Chem. Soc. 1994, 116, 12073-12074. (g) Madsen, R.; Udodong, U.; Roberts, C.; Mootoo, D.; Mootoo, U. D. R.; Konradsson, P.; Fraser-Reid, B. Studies related to Synthesis of Glycophosphatidylinositol Membrane-Bound Protein Anchors. 6. Convergent Assembly of Subunits. J. Am. Chem. Soc. 1995, 117, 1554-1565. (h) Tsukida, T.; Yoshida, M.; Kurokawa, K.; Nakai, Y.; Achiha, T.; Kiyoi, T.; Kondo, H. A Highly Practical Synthesis of Sulfated Lewis X: One-Pot, Two-Step Glycosylation Using "Armed/Disarmed" Coupling and Selective Benzoylation and Sulfation. J. Org. Chem. 1997, 62, 6876-6881.
14. For recent examples of elegant strategies for oligosaccharide synthesis, see: (a) Kondo, H.; Ichikawa, Y.; Wong, C.-H. β-Sialyl Phosphite and Phosphoramidite: Synthesis and Application to the Chemoenzymatic Synthesis of CMP-Sialic Acid and Sialyl Oligosaccharides. J. Am. Chem. Soc. 1992, 114, 8748-8750. (b) Halcomb, R. L.; Huang, H.; Wong, C.-H. Solution- and Solid-Phase Synthesis of Inhibitors of H. Pylori Attachment and E-Selectin-Mediated Leukocyte Adhesion. J. Am. Chem. Soc. 1994, 116, 11315-11322. (c) Mehta, S.; Pinto, B. M. Novel Glycosidation Methodology; The Use of Phenyl Selenoglycosides as Glycosyl Donors and Acceptors in Oligosaccharide Synthesis. J. Org. Chem. 1993, 58, 3269-3276. (d) Raghavan, S.; Kahne, D. A One-Step Synthesis of the Ciclamycin Trisaccharide. J. Am. Chem. Soc. 1993, 115, 1580-1581. (e) Yamada, H.; Harada, T.; Takahashi, T. Synthesis of an Elicitor-Active Hexaglucoside Analogue by a One-Pot, Two-Step Glycosidation Procedure. J. Am. Chem. Soc. 1994, 116, 7919-7920. (f) Kanie, O.; Ito, Y.; Ogawa, T. Orthogonal Glycosylation Strategy in Oligosaccharide Synthesis. J. Am. Chem. Soc. 1994, 116, 12073-12074. (g) Madsen, R.; Udodong, U.; Roberts, C.; Mootoo, D.; Mootoo, U. D. R.; Konradsson, P.; Fraser-Reid, B. Studies related to Synthesis of Glycophosphatidylinositol Membrane-Bound Protein Anchors. 6. Convergent Assembly of Subunits. J. Am. Chem. Soc. 1995, 117, 1554-1565. (h) Tsukida, T.; Yoshida, M.; Kurokawa, K.; Nakai, Y.; Achiha, T.; Kiyoi, T.; Kondo, H. A Highly Practical Synthesis of Sulfated Lewis X: One-Pot, Two-Step Glycosylation Using "Armed/Disarmed" Coupling and Selective Benzoylation and Sulfation. J. Org. Chem. 1997, 62, 6876-6881.
15. For recent examples of elegant strategies for oligosaccharide synthesis, see: (a) Kondo, H.; Ichikawa, Y.; Wong, C.-H. β-Sialyl Phosphite and Phosphoramidite: Synthesis and Application to the Chemoenzymatic Synthesis of CMP-Sialic Acid and Sialyl Oligosaccharides. J. Am. Chem. Soc. 1992, 114, 8748-8750. (b) Halcomb, R. L.; Huang, H.; Wong, C.-H. Solution- and Solid-Phase Synthesis of Inhibitors of H. Pylori Attachment and E-Selectin-Mediated Leukocyte Adhesion. J. Am. Chem. Soc. 1994, 116, 11315-11322. (c) Mehta, S.; Pinto, B. M. Novel Glycosidation Methodology; The Use of Phenyl Selenoglycosides as Glycosyl Donors and Acceptors in Oligosaccharide Synthesis. J. Org. Chem. 1993, 58, 3269-3276. (d) Raghavan, S.; Kahne, D. A One-Step Synthesis of the Ciclamycin Trisaccharide. J. Am. Chem. Soc. 1993, 115, 1580-1581. (e) Yamada, H.; Harada, T.; Takahashi, T. Synthesis of an Elicitor-Active Hexaglucoside Analogue by a One-Pot, Two-Step Glycosidation Procedure. J. Am. Chem. Soc. 1994, 116, 7919-7920. (f) Kanie, O.; Ito, Y.; Ogawa, T. Orthogonal Glycosylation Strategy in Oligosaccharide Synthesis. J. Am. Chem. Soc. 1994, 116, 12073-12074. (g) Madsen, R.; Udodong, U.; Roberts, C.; Mootoo, D.; Mootoo, U. D. R.; Konradsson, P.; Fraser-Reid, B. Studies related to Synthesis of Glycophosphatidylinositol Membrane-Bound Protein Anchors. 6. Convergent Assembly of Subunits. J. Am. Chem. Soc. 1995, 117, 1554-1565. (h) Tsukida, T.; Yoshida, M.; Kurokawa, K.; Nakai, Y.; Achiha, T.; Kiyoi, T.; Kondo, H. A Highly Practical Synthesis of Sulfated Lewis X: One-Pot, Two-Step Glycosylation Using "Armed/Disarmed" Coupling and Selective Benzoylation and Sulfation. J. Org. Chem. 1997, 62, 6876-6881.
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