Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes
- 作者：Fan ; Gang-Ting ; Pan ; Yi-shin ; Lu ; Kuo-Cheng ; Cheng ; Yu-Pei ; Lin ; Wan-Chen ; Lin ; Steven ; Lin ; Chun-Hung ; et. al.
- 关键词：Phytosphingosine ; α ; -Galactosyl ceramide ; Immuno stimulator ; Glycolipid
- 刊名：Tetrahedron
- 出版年：2005
- 期刊代码：107_00404020
- 类别：ch
- 出版时间：February 14, 2005
- 卷：61
- 期：7
- 页码：1855-1862
- 文件大小：663 K
摘要
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.