Synthesis and biological activity of α-glucosyl C24:0 and C20:2 ceramides |
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Authors: | Peter J Jervis Natacha Veerapen Gabriel Bricard Liam R Cox Steven A Porcelli Gurdyal S Besra |
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Institution: | 1. School of Biosciences, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK;2. School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK;3. Department of Microbiology and Immunology, Albert Einstein College of Medicine, Yeshiva University, Bronx, NY 10461, USA |
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Abstract: | α-Glucosyl ceramides 4 and 5 have been synthesised and evaluated for their ability to stimulate the activation and expansion of human iNKT cells. The key challenge in the synthesis of both target molecules was the stereoselective synthesis of the α-glycosidic linkage. Of the methods examined, glycosylation using per-TMS-protected glucosyl iodide 16 was completely α-selective and provided gram quantities of amine 11, from which α-glucosyl ceramides 4 and 5 were obtained by N-acylation. α-GlcCer 4, containing a C24 saturated acyl chain, stimulated a marked proliferation and expansion of human circulating iNKT cells in short-term cultures. α-GlcCer 5, which contains a C20 11,14-cis-diene acyl chain (C20:2), induced extremely similar levels of iNKT cell activation and expansion. |
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