TY - JOUR
T1 - CD1a-binding glycosphingolipids stimulating human autoreactive T-cells
T2 - Synthesis of a family of sulfatides differing in the acyl chain moiety
AU - Compostella, Federica
AU - Franchini, Laura
AU - De Libero, Gennaro
AU - Palmisano, Giovanni
AU - Ronchetti, Fiamma
AU - Panza, Luigi
N1 - Funding Information:
This work was supported by the University of Milano, the University of Piemonte Orientale, the MIUR, the Swiss National Found (grant NF 3100-055698.98), Human Frontier Science Program (grant RG0168/2000-M), and The Swiss Multiple Sclerosis Society.
PY - 2002/10/21
Y1 - 2002/10/21
N2 - 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.
AB - 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.
KW - Antigens
KW - Azidosphingosine
KW - Biologically active compounds
KW - Glycolipids
UR - http://www.scopus.com/inward/record.url?scp=0037152548&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(02)01092-X
DO - 10.1016/S0040-4020(02)01092-X
M3 - Article
SN - 0040-4020
VL - 58
SP - 8703
EP - 8708
JO - Tetrahedron
JF - Tetrahedron
IS - 43
ER -