848827-40-7Relevant academic research and scientific papers
Synthesis and biological activity of α-l-fucosyl ceramides, analogues of the potent agonist, α-d-galactosyl ceramide KRN7000
Veerapen, Natacha,Reddington, Faye,Bricard, Gabriel,Porcelli, Steven A.,Besra, Gurdyal S.
scheme or table, p. 3223 - 3226 (2010/09/04)
Several l-fucoglycolipids are associated with diseases such as cancer, cystic fibrosis and rheumatoid arthritis. Activation of iNKT cells is known to lead to the production of cytokines that can help alleviate or exacerbate these conditions. α-Galactosyl ceramide (α-GalCer) is a known agonist of iNKT cells and it is believed that its fucosyl counterpart might have similar immunogenic properties. We herein report the synthesis of α-l-fucosyl ceramide derivatives and describe their biological evaluation. The key challenge in the synthesis of the target molecules involved the stereoselective synthesis of the α-glycosidic linkage. Of the methods examined, the per-TMS-protected glycosyl iodide donor was completely α-selective, and could be scaled up to provide gram quantities of the azide precursor 11, from which a range of N-acylated α-l-fucosyl ceramides were readily obtained and evaluated for ex vivo expansion of human iNKT cells.
Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes
Fan, Gang-Ting,Pan, Yi-Shin,Lu, Kuo-Cheng,Cheng, Yu-Pei,Lin, Wan-Chen,Lin, Steven,Lin, Chun-Hung,Wong, Chi-Huey,Fang, Jim-Min,Lin, Chun-Cheng
, p. 1855 - 1862 (2007/10/03)
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
