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Shiro Komba, Masanori Yamaguchi, Hideharu Ishida, Makoto Kiso

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-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 ? 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).

Biological Chemistry, Walter de Gruyter

Print ISSN: 1431-6730
Volume: 382, 03/2001
Pages: 233 - 240

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