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Synthesis and biological activity of α-glucosyl C24:0 and C20:2 ceramides

Jervis, Peter J. and Veerapen, Natacha and Bricard, Gabriel and Cox, Liam R. and Porcelli, Steven A. and Besra, Gurdyal S. (2010) Synthesis and biological activity of α-glucosyl C24:0 and C20:2 ceramides. Bioorganic & Medicinal Chemistry Letters, 20 (12). p. 3475. ISSN 0960-894X

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URL of Published Version: http://dx.doi.org/10.1016/j.bmcl.2010.05.010

Identification Number/DOI: doi:10.1016/j.bmcl.2010.05.010

a-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 a-glycosidic linkage. Of the methods examined, glycosylation using per-TMS-protected glucosyl iodide 16 was completely a-selective and provided gram quantities of amine 11, from which a-glucosyl ceramides 4 and 5 were obtained by N-acylation. a-GlcCer 4, containing a C24 saturated acyl chain, stimulated a marked proliferation and expansion of human circulating iNKT cells in short-term cultures. a-GlcCer 5, which contains a C20 11,14-cis-diene acyl chain (C20:2),induced extremely similar levels of iNKT cell activation and expansion.

Type of Work:Article
Date:2010 (Publication)
School/Faculty:Colleges (2008 onwards) > College of Life & Environmental Sciences
Department:School of Biosciences
Subjects:QP Physiology
Institution:University of Birmingham
Copyright Holders:Elsevier
ID Code:408
Refereed:YES
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