6-O-sulfo de-N-acetylsialyl Lewis X as a novel high-affinity ligand for human L-selectin: total synthesis and structural characterization.
Total synthesis and structural characterization of a novel 6-O-sulfo de-N-acetylsialyl Lewis X, which was originally discovered as a minor by-product of the parent 6-O-sulfo N-acetylsialyl Lewis X, a high-affinity endogenous ligand for human L-selectin, are described. The total synthesis has been achieved by a highly efficient, regio- and alpha-stereoselective glycosylation of N-trifluoroacetylneuraminic acid, selective protections of the 3- and 6-hydroxyl groups of N-acetylglucosamine that undergo fucosylation and sulfation, and construction of the glycolipid structure containing a ceramide. The structure of 6-O-sulfo de-N-acetylsialyl Lewis X ganglioside was characterized by fast atom bombardment mass spectrometry (FAB-MS).
Komba
S
S
Department of Applied Bioorganic Chemistry, Gifu University, Japan.
Yamaguchi
M
M
Ishida
H
H
Kiso
M
M
D002240:Carbohydrate Sequence; D006801:Humans; D019041:L-Selectin / Q000378:metabolism*; D016256:Lewis X Antigen / Q000737:chemistry*; D008024:Ligands; D008969:Molecular Sequence Data; D000080506:Sialyl Lewis X Antigen / Q000031:analogs & derivatives; D016339:Spectrometry, Mass, Fast Atom Bombardment
C433828:6-O-sulfo de-N-acetylsialyl Lewis X; D016256:Lewis X Antigen; D008024:Ligands; D000080506:Sialyl Lewis X Antigen; D019041:L-Selectin