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

By Natacha Veerapen, Manfred Brigl, Salil Garg, Vincenzo Cerundolo, Liam R. Cox, M. B. Brenner and Gurdyal S Besra


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

Topics: Q Science (General), QD Chemistry
Publisher: Elsevier
Year: 2009
DOI identifier: 10.1016/j.bmcl.2009.05.095
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