E and Z α-C-galactosylceramides by Julia-Lythgoe-Kocienski chemistry:: A test of the receptor-binding model for glycolipid immunostimulants

Does aglycone linker conformation matter? Both E- and Z-linked α-C-galactosylceramides have been prepared by application of the Julia-Lythgoe-Kocienski synthesis to a C-formylgalactose and sulfones derived from phytosphingosine. Assays of cytokine levels induced by GalCers in mice suggest that the E geometry better resembles the preferred conformations of the flexible, saturated C-glycoside and the O-glycoside when bound to the CD1d molecule of antigen-presenting cells. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.