Search

Abstract: A concise synthesis of α-sulfatide 1, an analogue of natural glycolipid antigens with potential anti-tumor activity, was performed. Two different approaches to the α-glycosidic bond were explored, resulting in a high yield and excellent stereoselectivity. Compound 1 combines the structural features of sulfated β-GalCer (sulfatide) and α-GalCer, which activate specific T cells. α-Sulfatide 1 was stimulatory for CD1d-restricted semi-invariant Natural Killer T (iNKT) cell clones, although less potent than α-GalCer, while it was not recognized by CD1a-restricted sulfatide-specific T cells. [Copyright &y& Elsevier]

Abstract: Two novel hybrid molecules 3-O-sulfo-α/β-galactosylceramide 3 and 4, which are derived from an immunostimulatory agent α-GalCer 1 and self-glycolipid ligand sulfatide 2, were designed and synthesized. Compound 3 was shown to efficiently stimulate human NKT cells to secret IL-4 and IFN-γ, with activities similar to 1, suggesting that modification of the 3″-OH position of the galactose moiety with sulfate has no significant effect on NKT cell stimulation. As a comparison, the β-isomer 4 has no affinity to NKT cells, which demonstrates that the α-glycosidic bond of galactosylceramide is crucial to the NKT cells activation. [Copyright &y& Elsevier]