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-a cetylsialyl 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 ac hieved by a highly efficient, regio- and alpha -stereoseiective glycosylati on of N-trifluoroacetylneuraminic acid, selective protections of the 3- and 6-hydroxyl groups of N-acetylglucosamine that undergo fucosylation and sul fation, and construction of the glycolipid structure containing a ceramide, The structure of 6-O-sulfo de-N-acetylsialyl Lewis X ganglioside was chara cterized by fast atom bombardment mass spectrometry (FAB-MS).