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Synthesis and biological activity of α-galactosyl ceramide KRN7000 and galactosyl (α1→2) galactosyl ceramide

Veerapen, Natacha and Brigl, Manfred and Garg, Salil and Cerundolo, Vincenzo and Cox, Liam R. and Brenner, M. B. and Besra, Gurdyal S (2009) Synthesis and biological activity of α-galactosyl ceramide KRN7000 and galactosyl (α1→2) galactosyl ceramide. Bioorganic & Medicinal Chemistry Letters, 19 (15). pp. 4288-4291. ISSN 0960-894X

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URL of Published Version: http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pubmed&pubmedid=19502056

Identification Number/DOI: 10.1016/j.bmcl.2009.05.095

We herein report a faster and less cumbersome synthesis of the biologically attractive, α-galactosyl ceramide (α-GalCer), known as KRN7000, and its analogues. More importantly, the use of a silicon tethered intramolecular glycosylation reaction gave easy access to the diglycosyl ceramide Gal(α1→2)GalCer, which has been shown to require uptake and processing to the biologically active α-GalCer derivative.

Type of Work:Article
Date:01 August 2009 (Publication)
School/Faculty:Colleges (2008 onwards) > College of Life & Environmental Sciences
Department:School of Biosciences
Subjects:Q Science (General)
QD Chemistry
Institution:University of Birmingham
Copyright Holders:Elsevier
ID Code:239
Refereed:YES
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