Synthesis of alpha-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes

Abstract

Phytosphingosine and its short-chain analog were efficiently synthesized with 19% overall yield in 10 steps, respectively, starting from an inexpensive D-lyxose. Galactosyl donors of sulfide and phosphite types bearing benzoyl protecting groups of 4- and 6OH underwent glycosylation in excellent alpha-anomeric selectivity. A variety of alpha-galactosyl, fucosyl and glucosyl ceramides and serine-type lipids were prepared, and their activities involved in the proliferation of mouse splenocytes and the expression of cytokines were elucidated. Besides alpha-galactosyl ceramides, a galactosyl serine-type lipid also exhibited substantial effect on the expression of cytokines IFN-gamma and IL-4. (C) 2004 Elsevier Ltd. All rights reserved.