CD1a-binding glycosphingolipids stimulating human autoreactive T-cells: Synthesis of a family of sulfatides differing in the acyl chain moiety

Federica Compostella, Laura Franchini, Gennaro De Libero, Giovanni Palmisano, Fiamma Ronchetti, Luigi Panza

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

Native sulfatide (a mixture of 3-sulfated β-D-galactopyranosylceramides with different fatty acids at the ceramide moiety) is an antigen presented by CD1a proteins. Herein the preparation of four sulfatides, which are constituents of the natural mixture and bear palmitic, stearic, behenic or nervonic fatty acid chains, is described. Azidosphingosine was stereoselectively synthesized through a CuCN-catalyzed allylic alkylation of a hexenitol dimesylate derived from D-xylose; β-glycosylation of azidosphingosine with a suitable D-galactosyl trichloroacetimidate led, after reduction of the azido group, to the galactosylsphingosine skeleton, which was derivatized with the different fatty acids. Final regioselective 3-sulfation gave the desired sulfatides, which were tested for activation of sulfatide-specific and CD1a-restricted T-cell clones.

Lingua originaleInglese
pagine (da-a)8703-8708
Numero di pagine6
RivistaTetrahedron
Volume58
Numero di pubblicazione43
DOI
Stato di pubblicazionePubblicato - 21 ott 2002

Fingerprint

Entra nei temi di ricerca di 'CD1a-binding glycosphingolipids stimulating human autoreactive T-cells: Synthesis of a family of sulfatides differing in the acyl chain moiety'. Insieme formano una fingerprint unica.

Cita questo