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Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes |
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| Authors: | Gang-Ting Fan Yi-shin Pan Yu-Pei Cheng Steven Lin Chi-Huey Wong Jim-Min Fang Chun-Cheng Lin |
| Institution: | a Institute of Chemistry and Genomic Research Center, Academia Sinica, Nankang, Taipei 115, Taiwan, ROC b Department of Chemistry, National Taiwan University, Taipei 106, Taiwan, ROC c Institute of Biological Chemistry, Academia Sinica, Nankang, Taipei 115, Taiwan, ROC d Department of Applied Chemistry, National Chiao Tung University, Hsinchu 300, Taiwan, ROC |
| 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 6-OH underwent glycosylation in excellent α-anomeric selectivity. A variety of α-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 α-galactosyl ceramides, a galactosyl serine-type lipid also exhibited substantial effect on the expression of cytokines IFN-γ and IL-4. |
| Keywords: | Phytosphingosine α-Galactosyl ceramide Immuno stimulator Glycolipid |
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