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Synthesis and biological activity of α-l-fucosyl ceramides, analogues of the potent agonist, α-d-galactosyl ceramide KRN7000

Veerapen, Natacha and Reddington, Faye and Bricard, Gabriel and Porcelli, Steven A. and Besra, Gurdyal S. (2010) Synthesis and biological activity of α-l-fucosyl ceramides, analogues of the potent agonist, α-d-galactosyl ceramide KRN7000. Bioorganic & Medicinal Chemistry Letters, 20 (11). p. 3223. ISSN 0960894X

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URL of Published Version: http://dx.doi.org/10.1016/j.bmcl.2010.04.079

Identification Number/DOI: doi:10.1016/j.bmcl.2010.04.079

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. a-Galactosyl ceramide (a-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 a-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 a-glycosidic linkage. Of the methods examined, the per-TMS-protected glycosyl iodide donor was completely aselective,and could be scaled up to provide gram quantities of the azide precursor 11, from which a range of N-acylated a-L-fucosyl ceramides were readily obtained and evaluated for ex vivo expansion of human iNKT cells.

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:409
Refereed:YES
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