Selectin inhibition: synthesis and evaluation of novel sialylated, sulfated and fucosylated oligosaccharides, including the major capping group of GlyCAM-1.

No abstract is available for this paper.

• Publication year

  1997

• Venue

  Glycobiology

• Publication date

  1997-02-01

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1093/GLYCOB/7.1.79PMID 9061367
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Subsets of sialylated, sulfated mucins of diverse origins are recognized by L-selectin. Lack of evidence for unique oligosaccharide sequences mediating binding.

  1996cited by this paper
• Monosialogangliosides of human myelogenous leukemia HL60 cells and normal human leukocytes. 2. Characterization of E-selectin binding fractions, and structural requirements for physiological binding to E-selectin.

  1996cited by this paper
• Post-translational Modifications of Recombinant P-selectin Glycoprotein Ligand-1 Required for Binding to P- and E-selectin (*)

  1996cited by this paper
• Calcium-dependent oligonucleotide antagonists specific for L-selectin.

  1996cited by this paper
• Selectin ligands: 2,3,4-tri-O-acetyl-6-O-pivaloyl-α/β-galactopyranosyl halide as novel glycosyl donor for the synthesis of 3-O-sialyl or 3-O-sulfo Lex and Lea type structures

  1996cited by this paper
• Myeloglycan, a series of E-selectin-binding polylactosaminolipids found in normal human leukocytes and myelocytic leukemia HL60 cells.

  1995cited by this paper
• Selective modulation of the expression of L-selectin ligands by an immune response.

  1995cited by this paper
• Selectin-Saccharide Interactions: Revealing Structure-Function Relationships with Chemical Synthesis

  1995cited by this paper
• Ligand Recognition by E-Selectin: Synthesis, Inhibitory Activity and Conformational Analysis of Bivalent Sialyl Lewis x Analogs

  1995cited by this paper
• A sulfated peptide segment at the amino terminus of PSGL-1 is critical for P-selectin binding.

  1995cited by this paper
• Selectin-carbohydrate interactions and the initiation of the inflammatory response.

  1995cited by this paper
• Biosynthesis of GlyCAM-1, a Mucin-like Ligand for L-Selectin (*)

  1995cited by this paper
• Leukocyte trafficking mediated by selectin-carbohydrate interactions

  1995cited by this paper
• Peptides Which Bind to E-selectin and Block Neutrophil Adhesion (*)

  1995cited by this paper
• Recognition of consensus CHO structure in ligands for selectins by novel antibody against sialyl Lewis X.

  1995cited by this paper
• Structure of the O-Glycans in GlyCAM-1, an Endothelial-derived Ligand for L-selectin

  1995influential reference
• Sulfated disaccharide inhibitors of L-selectin: deriving structural leads from a physiological selectin ligand.

  1995cited by this paper
• The convergence‐divergence duality in lectin domains of selectin family and its implications

  1995cited by this paper
• Binding of sialyl Lewis x to E-selectin as measured by fluorescence polarization.

  1995cited by this paper
• Selectin ligands and tumor-associated carbohydrate structures: specificities of alpha 2,3-sialyltransferases in the assembly of 3'-sialyl-6-sialyl/sulfo Lewis a and x, 3'-sialyl-6'-sulfo Lewis x, and 3'-sialyl-6-sialyl/sulfo blood group T-hapten.

  1995cited by this paper
• Differential colon cancer cell adhesion to E-, P-, and L-selectin: role of mucin-type glycoproteins.

  1995cited by this paper
• Characterization of a novel mucin sulphotransferase activity synthesizing sulphated O-glycan core 1, 3-sulphate-Galβ1-3GalNAcα-R

  1995cited by this paper
• De novo expression of endothelial sialyl Lewis(a) and sialyl Lewis(x) during cardiac transplant rejection: superior capacity of a tetravalent sialyl Lewis(x) oligosaccharide in inhibiting L-selectin-dependent lymphocyte adhesion

  1995cited by this paper
• Tyrosine Sulfation of P-selectin Glycoprotein Ligand-1 Is Required for High Affinity Binding to P-selectin (*)

  1995influential reference
• Synthesis of a divalent sialyl Lewis x O-glycan, a potent inhibitor of lymphocyte-endothelium adhesion. Evidence that multivalency enhances the saccharide binding to L-selectin.

  1995cited by this paper
• PSGL-1 recognition of P-selectin is controlled by a tyrosine sulfation consensus at the PSGL-1 amino terminus.

  1995cited by this paper
• Characterization of a novel mucin sulphotransferase activity synthesizing sulphated O-glycan core 1,3-sulphate-Gal beta 1-3GalNAc alpha-R.

  1995cited by this paper
• Insight into E-selectin/ligand interaction from the crystal structure and mutagenesis of the lec/EGF domains

  1994cited by this paper
• Adhesion molecules and inflammatory injury

  1994cited by this paper
• Isolation and characterization of natural protein-associated carbohydrate ligands for E-selectin.

  1994cited by this paper
• Multivalent sialyl-LeX: potent inhibitors of E-selectin-mediated cell adhesion; reagent for staining activated endothelial cells.

  1994cited by this paper
• A liquid-phase binding analysis for L-selectin. A strong dependency on highly clustered sulfate groups.

  1994cited by this paper
• The soluble form of E-selectin is an asymmetric monomer. Expression, purification, and characterization of the recombinant protein.

  1994cited by this paper
• Endothelial-leukocyte adhesion molecules in human disease.

  1994cited by this paper
• Sulfated blood group Lewis(a). A superior oligosaccharide ligand for human E-selectin.

  1994cited by this paper
• Identification of the sulfated monosaccharides of GlyCAM-1, an endothelial-derived ligand for L-selectin.

  1994cited by this paper
• 6'-sulfated sialyl Lewis x is a major capping group of GlyCAM-1.

  1994cited by this paper
• Enzymatic synthesis of a 6'-sulphated sialyl-Lewisx which is an inhibitor of L-selectin binding to peripheral addressin.

  1994cited by this paper
• Role of selectins, a new family of adhesion molecules, in ischaemia-reperfusion injury.

  1994cited by this paper
• Sialylation and sulfation of the carbohydrate chains in respiratory mucins from a patient with cystic fibrosis.

  1994cited by this paper
• Selectin ligands.

  1994cited by this paper
• The selectins and their ligands.

  1994cited by this paper
• Sialyl Lewis X mimics derived from a pharmacophore search are selectin inhibitors with anti-inflammatory activity.

  1994cited by this paper
• Characterization of a specific ligand for P-selectin on myeloid cells. A minor glycoprotein with sialylated O-linked oligosaccharides.

  1993cited by this paper
• Heparin oligosaccharides bind L- and P-selectin and inhibit acute inflammation.

  1993cited by this paper
• Higher-affinity oligosaccharide ligands for E-selectin.

  1993cited by this paper
• Expression cloning of a functional glycoprotein ligand for P-selectin.

  1993cited by this paper
• Structure-function studies on selectin carbohydrate ligands. Modifications to fucose, sialic acid and sulphate as a sialic acid replacement.

  1993cited by this paper
• Structural and functional characterization of monomeric soluble P-selectin and comparison with membrane P-selectin.

  1993influential reference
• L-selectin-mediated lymphocyte rolling on MAdCAM-1

  1993cited by this paper
• Calcium-dependent heparin-like ligands for L-selectin in nonlymphoid endothelial cells.

  1993cited by this paper
• Selectins.

  1993cited by this paper
• Enhanced interaction of L-selectin with the high endothelial venule ligand via selectively oxidized sialic acids.

  1993cited by this paper
• First synthesis of the 3′-sulfated Lewis trisaccharide, putative ligand for the leucocyte homing receptor

  1993cited by this paper
• Binding of L-selectin to the vascular sialomucin CD34.

  1993cited by this paper
• Direct demonstration of heterogeneous, sulfatedO-linked carbohydrate chains on an endothelial ligand for L-selectin

  1993cited by this paper
• P- and E-selectin use common sites for carbohydrate ligand recognition and cell adhesion

  1993cited by this paper
• Interaction of P-selectin (CD62) and its cellular ligand: analysis of critical residues.

  1993cited by this paper
• Oligosaccharide structures of mucins secreted by the human colonic cancer cell line CL.16E.

  1992cited by this paper
• Biochemistry of carbohydrate‐protein interaction 1

  1992cited by this paper
• An endothelial ligand for L-selectin is a novel mucin-like molecule.

  1992cited by this paper
• Identification of a specific glycoprotein ligand for P-selectin (CD62) on myeloid cells

  1992cited by this paper
• Further characterization of the interaction between L-selectin and its endothelial ligands.

  1992cited by this paper
• Identification of an E-selectin region critical for carbohydrate recognition and cell adhesion [published erratum appears in J Cell Biol 1993 Feb;120(4):1071]

  1992cited by this paper
• Structural analysis of monosulfated side-chain oligosaccharides isolated from human tracheobronchial mucous glycoproteins.

  1992cited by this paper
• Total synthesis of sialyl dimeric Lex

  1992cited by this paper
• Mucin-type glycoproteins.

  1992cited by this paper
• The glycoprotease of Pasteurella haemolytica A1 eliminates binding of myeloid cells to P-selectin but not to E-selectin.

  1992cited by this paper
• Purification and characterization of GDP-L-Fuc-N-acetyl-beta-D-glucosaminide alpha 1----3fucosyltransferase from human neuroblastoma cells. Unusual substrate specificities of the tumor enzyme.

  1991cited by this paper
• Interterminal distance and flexibility of a triantennary glycopeptide as measured by resonance energy transfer.

  1991cited by this paper
• A carbohydrate domain common to both sialyl Le(a) and sialyl Le(X) is recognized by the endothelial cell leukocyte adhesion molecule ELAM-1.

  1991cited by this paper
• Identification of a carbohydrate-based endothelial ligand for a lymphocyte homing receptor

  1991cited by this paper
• Iodonium ion promoted reactions at the anomeric centre. II An efficient thioglycoside mediated approach toward the formation of 1,2-trans linked glycosides and glycosidic esters

  1990cited by this paper
• Synthesis of the sodium salts of methyl 2-O-alpha-L-fucopyranosyl-alpha-L-fucopyranoside 3- and 4-sulfate.

  1990cited by this paper
• Synthesis of the sodium salts of methyl 2-O-α-l-fucopyranosyl-α-l-fucopyranoside 3- and 4-sulfate

  1990cited by this paper
• Defined geometry of binding between triantennary glycopeptide and the asialoglycoprotein receptor of rat heptocytes.

  1990cited by this paper
• Stereoselective synthesis of 2-thioglycosides of N-acetylneuraminic acid

  1989cited by this paper
• Characterization of human platelet GMP-140 as a heparin-binding protein.

  1989cited by this paper
• Synthesis of a dimeric Lewis X hexasaccharide derivative corresponding to a tumor-associated glycolipid.

  1988cited by this paper
• The GDP-fucose:N-acetylglucosaminide 3-alpha-L-fucosyltransferases of LEC11 and LEC12 Chinese hamster ovary mutants exhibit novel specificities for glycolipid substrates.

  1987cited by this paper
• Total synthesis of X hapten, III3 Fuc alpha-nLc4 Cer.

  1987cited by this paper
• An efficient approach to O-glycosides through CuBr2-Bu4NBr mediated activation of glycosides

  1986cited by this paper
• Synthesis of methyl O-(3-deoxy-3-fluoro-beta-D-galactopyranosyl)-(1----6)-O-beta-D- galactopyranosyl-(1----6)-3-deoxy-3-fluoro-beta-D-galactopyranoside and related N.M.R. studies.

  1985cited by this paper
• Synthesis of methyl O-(3-deoxy-3-fluoro-β-?-galactopyranosyl)-(1→6)-O-β-?-galactopyranosyl-(1→6)-3-deoxy-3-fluoro -β-?-galactopyranoside and related n.m.r. studies

  1985cited by this paper
• Synthetic mucin fragments: benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-beta- D-glucopyranosyl)-2-deoxy-3-O-beta-D-galactopyranosyl-alpha-D- galactopyranoside and benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)- 3-O-[6-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-beta-D- galactopy

  1984cited by this paper
• AN EFFICIENT METHOD FOR GLUCOSYLATION OF HYDROXY COMPOUNDS USING GLUCOPYRANOSYL FLUORIDE

  1981cited by this paper
• Sialyl- and fucosyltransferases in the biosynthesis of asparaginyl-linked oligosaccharides in glycoproteins. Mutually exclusive glycosylation by beta-galactoside alpha2 goes to 6 sialyltransferase and N-acetylglucosaminide alpha1 goes to 3 fucosyltransferase.

  1978cited by this paper
• THE PROPERTIES OF A ′SYNTHETIC′ ANTIGEN RELATED TO THE HUMAN BLOOD-GROUP LEWIS A

  1975cited by this paper
• The properties of a "synthetic" antigen related to the human blood-group Lewis a.

  1975cited by this paper

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  2022cites this paper
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  2019cites this paper
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  2018cites this paper
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  2017cites this paper
• Targeting P‐selectin glycoprotein ligand‐1/P‐selectin interactions as a novel therapy for metabolic syndrome

  2017cites this paper
• Structural requirements of mono- and multivalent L-selectin blocking aptamers for enhanced receptor inhibition in vitro and in vivo.

  2016cites this paper
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  2016cites this paper
• Identification and characterisation of host-pathogen protein-protein interactions in the blood stages of malaria

  2015cites this paper
• Enhancing MS(n) mass spectrometry strategy for carbohydrate analysis: A b2 ion spectral library.

  2015cites this paper
• Targeting selectins for the treatment of inflammatory diseases

  2014cites this paper
• Strong and specific interaction of ultra small superparamagnetic iron oxide nanoparticles and human activated platelets mediated by fucoidan coating

  2014cites this paper
• Charakterisierung der L-Selektin–Ligand-Interaktion unter Fluss mittels biochemischer Modifikation und multivalenter Inhibitoren

  2014cites this paper
• Polyglycerolsulfate Functionalized Gold Nanorods as Optoacoustic Signal Nanoamplifiers for In Vivo Bioimaging of Rheumatoid Arthritis

  2014cites this paper
• Glycobiology of platelet-endothelial cell interactions.

  2014cites this paper
• Fucoidan interferes with Porphyromonas gingivalis-induced aneurysm enlargement by decreasing neutrophil activation.

  2013cites this paper
• KSGal6ST generates galactose-6-O-sulfate in high endothelial venules but does not contribute to L-selectin-dependent lymphocyte homing.

  2013cites this paper
• Contribute to L-Selectin Dependent Lymphocyte Homing

  2012cites this paper
• P-Selectin and Its Ligands

  2012cites this paper
• L-Selectin (CD62L) and Its Ligands

  2012cites this paper
• Synthesis of dendritic polyglycerol anions and their efficiency toward L-selectin inhibition.

  2011cites this paper
• The role of dimension in multivalent binding events: structure-activity relationship of dendritic polyglycerol sulfate binding to L-selectin in correlation with size and surface charge density.

  2011cites this paper
• Synthesis of hemagglutinin-binding trisaccharides.

  2011cites this paper
• Radiolabeled Fucoidan as a P-Selectin Targeting Agent for In Vivo Imaging of Platelet-Rich Thrombus and Endothelial Activation

  2011cites this paper
• Investigation of glycosylating properties of 1-deoxy-1-ethoxysulfonyl-hept-2-ulopyranosyl derivatives. Synthesis of a new sulfonic acid mimetic of the sialyl Lewis X tetrasaccharide.

  2011cites this paper
• Computational modeling of carbohydrate-recognition process in E-selectin complex: structural mapping of sialyl Lewis X onto ab initio QM/MM free energy surface.

  2010cites this paper
• Human L-selectin preferentially binds synthetic glycosulfopeptides modeled after endoglycan and containing tyrosine sulfate residues and sialyl Lewis x in core 2 O-glycans.

  2010cites this paper
• P-selectin antagonism in inflammatory disease.

  2010cites this paper
• Struktur und Funktion des Adhäsionsrezeptors L-Selektin

  2010influential citation
• Fluorescence-based solid-phase assays to study glycan-binding protein interactions with glycoconjugates.

  2010cites this paper
• 3'-Sulfo-Le(x) is important for regulation of integrin subunit alphaV.

  2010cites this paper
• Affinity of low molecular weight fucoidan for P-selectin triggers its binding to activated human platelets.

  2009cites this paper
• Glycoforms of human endothelial CD34 that bind L-selectin carry sulfated sialyl Lewis x capped O- and N-glycans.

  2009cites this paper
• Targeting selectins and selectin ligands in inflammation and cancer

  2007cites this paper
• P-selectin glycoprotein ligand-1 (PSGL-1)

  2007cites this paper
• CHAPTER 12 – P-Selectin/PSGL-1 and Other Interactions between Platelets, Leukocytes, and Endothelium

  2007cites this paper
• Synthesis and Characterization of Glycosides

  2006cites this paper
• Affinity and kinetics of sialyl Lewis-X and core-2 based oligosaccharides binding to L- and P-selectin.

  2005cites this paper
• Sialylation of the Gram-Negative Bacterial Cell Surface

  2005cites this paper
• Carbohydrate Mimetics in Drug Discovery

  2005cites this paper
• Transport Features, Reaction Kinetics and Receptor Biomechanics Controlling Selectin and Integrin Mediated Cell Adhesion

  2004cites this paper
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  2004cites this paper
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  2004cites this paper
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  2004cites this paper
• Molecular Mechanisms of Leukocyte Adhesion

  2003cites this paper
• Model Glycosulfopeptides from P-selectin Glycoprotein Ligand-1 Require Tyrosine Sulfation and a Core 2-branched O-Glycan to Bind to L-selectin*

  2003cites this paper
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  2003cites this paper
• Complex oligosaccharide investigations: synthesis of an octasaccharide incorporating the dimeric Le(x) structure of PSGL-1.

  2003cites this paper
• Selectin inhibitors

  2003cites this paper
• Detection of ligands for selectins in the oligosaccharide fraction of human milk

  2002cites this paper
• Design and synthesis of sialyl Lewisx mimics as E‐ and P‐selectin inhibitors

  2002cites this paper
• Affinity and kinetic analysis of L-selectin binding to their natural ligands and to synthetic oligosaccharides

  2002cites this paper
• Acquisition of potential N-glycosylation sites in the immunoglobulin variable region by somatic mutation is a distinctive feature of follicular lymphoma.

  2002cites this paper
• Liposomes Containing Ligands

  2002cites this paper
• Adhesive Interactions of Leukocytes, Platelets, and the Vessel Wall during Hemostasis and Inflammation

  2001cites this paper
• Sulfation of L-selectin ligands by an HEV-restricted sulfotransferase regulates lymphocyte homing to lymph nodes.

  2001cites this paper
• Minimal requirements for the binding of selectin ligands to a C-type carbohydrate-recognition domain.

  2001cites this paper
• Synthesis of a set of di- and tri-sulfated galabioses.

  2001cites this paper
• Enhanced 3-O-sulfation of galactose in Asn-linked glycans and Maackia amurensis lectin binding in a new Chinese hamster ovary cell line.

  2001cites this paper
• Polymerized liposome assemblies: bifunctional macromolecular selectin inhibitors mimicking physiological selectin ligands.

  2001cites this paper
• Chemical synthesis of a core 2 branched pentasaccharide containing a carboxylate group.

  2000cites this paper
• Minimal Sulfated Carbohydrates for Recognition by L-selectin and the MECA-79 Antibody*

  2000cites this paper
• Acquisition of P-selectin binding activity by en bloc transfer of sulfo Le(x) trisaccharide to the cell surface: comparison to a sialyl Le(x) tetrasaccharide transferred on the cell surface.

  2000cites this paper
• Structure of a C-type Carbohydrate Recognition Domain from the Macrophage Mannose Receptor*

  2000cites this paper
• CD164-A Novel Sialomucin on CD34+ Cells

  2000cites this paper
• Chemical synthesis of sulfated oligosaccharides with a β-d-Gal-(1→3)-[β-d-Gal-(1→4)-(α-l-Fuc-(1→3)-β-d-GlcNAc-(1→6)]-α-d-GalNAc sequence

  2000cites this paper
• First total synthesis of sialylated and sulfated Lewisx mucin Core 2 structures as potential tumor associated antigens

  2000cites this paper
• MINI REVIEW Carbohydrate sulfotransferases in lymphocyte homing

  2000cites this paper
• Chemical synthesis of sulfated oligosaccharides with a beta-D-Gal-(1-->3).

  2000cites this paper
• Binding of Glycosulfopeptides to P-selectin Requires Stereospecific Contributions of Individual Tyrosine Sulfate and Sugar Residues*

  2000cites this paper
• Neutrophil migration mechanisms, with an emphasis on the pulmonary vasculature.

  2000cites this paper
• Carbohydrate sulfotransferases in lymphocyte homing.

  2000cites this paper
• L-selectin Interactions with Novel Mono- and Multisulfated Lewisx Sequences in Comparison with the Potent Ligand 3′-Sulfated Lewisa *

  1999cites this paper
• Sulfotransferases of Two Specificities Function in the Reconstitution of High Endothelial Cell Ligands for L-selectin

  1999cites this paper
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  1999cites this paper
• Mechanisms that regulate the function of the selectins and their ligands.

  1999cites this paper
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  1999cites this paper
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  1999cites this paper
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  1999cites this paper
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  1999influential citation
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  1999cites this paper
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  1999cites this paper
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  1999cites this paper
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  1999cites this paper
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  1999cites this paper
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  1998cites this paper
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  1998cites this paper
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  1998cites this paper
• Identification of an N-acetylglucosamine-6-0-sulfotransferase activity specific to lymphoid tissue: an enzyme with a possible role in lymphocyte homing.

  1998cites this paper
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  1998cites this paper
• Affinity and Kinetic Analysis of P-selectin Binding to P-selectin Glycoprotein Ligand-1*

  1998cites this paper
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  1998cites this paper
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  1998cites this paper
• Inhibition of L- and P-selectin by a rationally synthesized novel core 2-like branched structure containing GalNAc-Lewisx and Neu5Acalpha2-3Galbeta1-3GalNAc sequences.

  1998cites this paper
• Novel synthetic inhibitors of selectin-mediated cell adhesion: synthesis of 1,6-bis[3-(3-carboxymethylphenyl)-4-(2-alpha-D- mannopyranosyloxy)phenyl]hexane (TBC1269).

  1998cites this paper
• SHORT SYNTHESIS OF SULFATIDE- AND SQDG-MIMETICS AS SMALL MOLECULAR WEIGHT SELECTIN INHIBITORS

  1998cites this paper
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  1998cites this paper
• Functional groups of sialic acids involved in binding to siglecs (sialoadhesins) deduced from interactions with synthetic analogues.

  1998cites this paper
• Fucosylation of Disaccharide Precursors of Sialyl LewisX Inhibit Selectin-mediated Cell Adhesion*

  1997cites this paper
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  1997cites this paper