Synthesis and Biological Activity of α-Galactosyl Ceramide KRN7000 and Galactosyl (α1→2) Galactosyl Ceramide

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

Abstract

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.

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