Synthesis of diglycosylceramides and evaluation of their iNKT cell stimulatory properties.

Bioorganic & Medicinal Chemistry Letters
Yang LiuPaul B Savage

Abstract

Stimulation of iNKT cells is highly dependent on the structures of the glycolipids presented by CD1d. Furthermore, antigen processing and CD1d loading in lysosomes play central roles in controlling the stimulatory properties of glycolipid antigens. Previously, we determined that substitution at C6'' on alpha-galactosylceramides did not significantly impact stimulatory properties; however, it was not known if substitution at this position influenced lysosomal processing of oligoglycosylceramides. We have prepared a series of mono- and di-galactosylceramides to observe the impact of C6'' substitution on glycosidase truncation of these glycolipids. We found that substitution did not significantly impact glycosidase activity or loading into CD1d.

References

Feb 7, 2001·Science·T I PrigozyM Kronenberg

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Citations

Dec 20, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Brian L AndersonPaul B Savage
Nov 26, 2015·Organic Letters·Benjamin J ComptonGavin F Painter
Jun 20, 2013·Chembiochem : a European Journal of Chemical Biology·Bridget L Stocker, Mattie S M Timmer
Mar 12, 2011·Organic & Biomolecular Chemistry·Aline Banchet-CadedduArnaud Haudrechy
Jul 17, 2012·The Journal of Immunology : Official Journal of the American Association of Immunologists·Richard M GalloRandy R Brutkiewicz

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