title: Studies on the endogenous L-selectin ligands: systematic and highly efficient total synthetic routes to lactamized-sialyl 6-O-sulfo Lewis X and other novel gangliosides containing lactamized neuraminic acid.
abstract: Systematic syntheses of lactamized neuraminic acid-containing gangliosides GM4, sulfated sialylparagloboside, and sulfated/nonsulfated sialyl Lewis X are described. The highly efficient, one-step lactamization of neuraminic acid was accomplished by treatment of the N-deacetylated sialic acid (neuraminic acid)-containing gangliosides with HBTU and HOBt in DMF at 65 degrees C. Both the lactamized neuraminic acid residue and the sulfate group at O-6 of the GlcNAc residue were found to be involved in the antigenic determinant defined by G159 monoclonal antibody, while the fucose residue may not be critical for the recognition by G159 mAb.
authors.affiliation: Department of Applied Bio-organic Chemistry, Gifu University, Gifu 501-1193, Japan.
authors.forename: Masanori
authors.initials: M
authors.lastname: Yamaguchi
authors.forename: Hideharu
authors.initials: H
authors.lastname: Ishida
authors.forename: Akiko
authors.initials: A
authors.lastname: Kanamori
authors.forename: Reiji
authors.initials: R
authors.lastname: Kannagi
authors.forename: Makoto
authors.initials: M
authors.lastname: Kiso
mesh_terms: D000911:Antibodies, Monoclonal / Q000737:chemistry; D002236:Carbohydrate Conformation; D002855:Chromatography, Thin Layer; D005732:Gangliosides / Q000737:chemistry; D005915:Globosides / Q000737:chemistry; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology; D006031:Glycosylation; D019041:L-Selectin / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000276:immunology; D016256:Lewis X Antigen / Q000031:analogs & derivatives; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D019158:N-Acetylneuraminic Acid / Q000737:chemistry; D009438:Neuraminic Acids / Q000737:chemistry; D009844:Oligosaccharides / Q000737:chemistry / Q000276:immunology; D025942:Oligosaccharides, Branched-Chain / Q000138:chemical synthesis; D000080506:Sialyl Lewis X Antigen / Q000031:analogs & derivatives
chemical_list: C086949:6'-sulfated sialyl Lewis x; D000911:Antibodies, Monoclonal; D005732:Gangliosides; D005915:Globosides; D006017:Glycolipids; D007769:Lactams; D016256:Lewis X Antigen; D008024:Ligands; D009438:Neuraminic Acids; D009844:Oligosaccharides; D025942:Oligosaccharides, Branched-Chain; D000080506:Sialyl Lewis X Antigen; D019041:L-Selectin; C036363:paragloboside; C028253:ganglioside, GM4; D019158:N-Acetylneuraminic Acid