Publication | Open Access
The First Total Synthesis of 6-Sulfo-de-N-acetylsialyl Lewisx Ganglioside: A Superior Ligand for Human L-Selectin
75
Citations
0
References
1999
Year
Bioorganic ChemistrySuperior LigandChemical BiologyPharmaceutical ChemistryMedicinal ChemistryExtraordinary ReactivityHuman L-selectinStereoselective Synthesis6-Sulfo-de-n-acetylsialyl Lewisx GangliosideBiochemistrySuperior L-selectin LigandVascular BiologyPharmacologyNatural Product SynthesisEnantioselective Synthesis6-Sulfo-n-acetylsialyl LewisFunctional SelectivityNatural SciencesMedicineDrug Discovery
Originally discovered as a minor by-product of 6-sulfo-N-acetylsialyl Lewis(x) , the de-N-acetylated form 1 is a superior L-selectin ligand to the N-acetyl form. To substantiate the extraordinary reactivity of 1, it was synthesized for the first time and its binding to L-selectin investigated. Compound 1 and related structures may be high-affinity endogenous ligands for L-selectin that are involved in the interaction of leukocytes with the vascular endothelium.