Synthesis and biological activity of alpha-L-fucosyl ceramides, analogues of the potent agonist, alpha-D-galactosyl ceramide KRN7000.
Bottom Line: Activation of iNKT cells is known to lead to the production of cytokines that can help alleviate or exacerbate these conditions. alpha-Galactosyl ceramide (alpha-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 alpha-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 alpha-glycosidic linkage.
Affiliation: School of Biosciences, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK.Show MeSH
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Mentions: Fan et al.25 reported the synthesis of compound 4d, while Okamoto et al.27 reported that of compound 4e. Both groups obtained their target compounds as an α, β mixture (3:1 ratio) from different glycosyl donors and acceptors (Scheme 1). On the other hand, in the original reported synthesis of the fucosylceramide 1, only the α-anomer was isolated when another ceramide acceptor was used under different reaction conditions.
Affiliation: School of Biosciences, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK.