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6-O-Sulfo De-N-Acetylsialyl Lewis X as a Novel High-Affinity Ligand for Human L-Selectin: Total Synthesis and Structural Characterization
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Shiro Komba
Published/Copyright:
June 1, 2005
Abstract
Total synthesis and structural characterization of a novel 6-Osulfo deNacetylsialyl Lewis X, which was originally discovered as a minor byproduct of the parent 6-Osulfo Nacetylsialyl Lewis X, a highaffinity endogenous ligand for human Lselectin, are described. The total synthesis has been achieved by a highly efficient, regio and α stereoselective glycosylation of Ntrifluoroacetylneuraminic acid, selective protections of the 3- and 6-hydroxyl groups of Nacetylglucosamine that undergo fucosylation and sulfation, and construction of the glycolipid structure containing a ceramide. The structure of 6-Osulfo deNacetylsialyl Lewis X ganglioside was characterized by fast atom bombardment mass spectrometry (FABMS).
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Published Online: 2005-06-01
Published in Print: 2001-02-12
Copyright © 2001 by Walter de Gruyter GmbH & Co. KG
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Articles in the same Issue
- Highlight: Glycobiology
- O-Glycosylation of the Mucin Type
- Glycoproteins from Insect Cells: Sialylated or Not?
- Congenital Disorders of Glycosylation: Glycosylation Defects in Man and Biological Models for Their Study
- Mitochondrial Single-Stranded DNA-Binding Proteins: in Search for New Functions
- Do Rodent and Human Brains Have Different N-Glycosylation Patterns?
- The Liver Flukes Fasciola gigantica and Fasciola hepatica Express the Leucocyte Cluster of Differentiation Marker CD77 (Globotriaosylceramide) in Their Tegument
- Cloning and Expression of Drosophila melanogaster UDP-GlcNAc:?-3-D-Mannoside ? 1,2-N-Acetylglucosaminyltransferase I
- Pathways of Mucin O-Glycosylation in Normal and Malignant Rat Colonic Epithelial Cells Reveal a Mechanism for Cancer-Associated Sialyl-Tn Antigen Expression
- 6-O-Sulfo De-N-Acetylsialyl Lewis X as a Novel High-Affinity Ligand for Human L-Selectin: Total Synthesis and Structural Characterization
- Segregation of Gangliosides GM1 and GD3 on Cell Membranes, Isolated Membrane Rafts, and Defined Supported Lipid Monolayers
- Structural Characterization of Fucose-Containing Oligosaccharides by High-Performance Liquid Chromatography and Matrix-Assisted Laser Desorption/ Ionization Time-of-Flight Mass Spectrometry
- Anencephaly: Structural Characterization of Gangliosides in Defined Brain Regions
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- Biosynthesis of N-Acetylneuraminic Acid in Cells Lacking UDP-N-Acetylglucosamine 2-Epimerase/ N-Acetylmannosamine Kinase
- Synthesis of Nucleotide-Activated Oligosaccharides by ?-Galactosidase from Bacillus circulans
- Elucidation of the Role of Functional Amino Acid Residues of the Small Sialidase from Clostridium perfringens by Site-Directed Mutagenesis
- Biosynthesis of Lipid-Linked Oligosaccharides in Yeast: the ALG3 Gene Encodes the Dol-P-Man:Man5GlcNAc2-PP-Dol Mannosyltransferase
- Intra- and Intermolecular Triplex DNA Formation in the Murine c-myb Proto-Oncogene Promoter Are Inhibited by Mithramycin
- Experimental Regulation of STAT Gene Expression Reveals an Involvement of STAT5 in Interleukin-4-Driven Cell Proliferation
