Tetrahedron

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

F Compostella, L Franchini, G De Libero, G Palmisano…

Index: Compostella, Federica; Franchini, Laura; De Libero, Gennaro; Palmisano, Giovanni; Ronchetti, Fiamma; Panza, Luigi Tetrahedron, 2002 , vol. 58, # 43 p. 8703 - 8708

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Citation Number: 34

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 ...

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