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.
Highlights
The thioglycoside 4 was obtained in large scale from commercially available β-Dgalactopyranose pentaacetate after standard procedures, as described previously.The critical glycosylation was attempted on 2 g of the donor 4
Target compound 1 was obtained as a white solid after concentration of the organic phase and purification of the residue by flash chromatography
Galactosidases from lysosomes are responsible for truncating oligoglycosyl ceramides to monoglycosyl ceramides before they can bind to CD1d and be presented to invariant Natural Killer T (iNKT) cells
Summary
Synthesis and biological activity of -galactosyl ceramide KRN7000 and galactosyl (12) galactosyl ceramide. Natacha; Brigl, M; Garg, S; Cerundolo, V; Cox, Liam; Brenner, MB; Besra, Gurdyal. Document Version Publisher's PDF, known as Version of record Citation for published version (Harvard): Veerapen, N, Brigl, M, Garg, S, Cerundolo, V, Cox, L, Brenner, MB & Besra, G 2009, 'Synthesis and biological activity of -galactosyl ceramide KRN7000 and galactosyl (12) galactosyl ceramide', Bioorganic & Medicinal Chemistry Letters, vol 19, no.
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