Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 20, Issue 12, Pages 3475-3478Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2010.05.010
Keywords
CD1d; iNKT; Antigen; Ceramide; Lipid
Categories
Funding
- Personal Research Chair
- Royal Society Wolfson Research Merit Award
- Lister Institute-Jenner Research Fellowship
- Medical Research Council
- The Wellcome Trust [084923/B/08/Z]
- NIH/NIAID [AI45889]
- Einstein Center for AIDS Research [AI 051519]
- Einstein Cancer Center [CA 13330]
- Birmingham Science City
- Advantage West Midlands (AWM)
- European Regional Development Fund (ERDF)
- MRC [G0400421] Funding Source: UKRI
- Medical Research Council [G0400421] Funding Source: researchfish
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alpha-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 alpha-glycosidic linkage. Of the methods examined, glycosylation using per-TMS-protected glucosyl iodide 16 was completely alpha-selective and provided gram quantities of amine 11, from which alpha-glucosyl ceramides 4 and 5 were obtained by N-acylation. alpha-GlcCer 4, containing a C24 saturated acyl chain, stimulated a marked proliferation and expansion of human circulating iNKT cells in short-term cultures. alpha-GlcCer 5, which contains a C20 11,14-cis-diene acyl chain (C20: 2), induced extremely similar levels of iNKT cell activation and expansion. (C) 2010 Elsevier Ltd. All rights reserved.
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