TY - JOUR
T1 - Synthesis of sulfated galactocerebrosides from an orthogonal β-D-galactosylceramide scaffold for the study of CD1-antigen interactions
AU - Compostella, Federica
AU - Ronchi, Silvia
AU - Panza, Luigi
AU - Mariotti, Sabrina
AU - Mori, Lucia
AU - De Libero, Gennaro
AU - Ronchetti, Fiamma
PY - 2006/7/17
Y1 - 2006/7/17
N2 - CD1a protein binds sulfatide (3-O-sulfo-β-D-galactosylceramide) to form an antigen complex that interacts with T cell receptors and activates T cells. To assess the role of the position of the sulfate in T cell activation, the synthesis of three β-D-galactosylceramides, variously bearing a sulfate at position 2, 4, or 6 of galactose, has been planned and carried out. The compounds were synthesized by an or thogonal sulfation strategy from a common β-o-galactosylceramide scaffold, which was in turn obtained through an efficient glycosylation reaction between a fully orthogonally protected galactosyl imidate and 3-O-ben zoylazidosphingosine. Immunological evaluation of the three sulfated compounds in CD 1a-mediated T cell activation, in comparison with natural sulfatide, provided evidence of the influence of the sulfate position in the recognition event between the antigen, the CD1 protein and the T cell receptor.
AB - CD1a protein binds sulfatide (3-O-sulfo-β-D-galactosylceramide) to form an antigen complex that interacts with T cell receptors and activates T cells. To assess the role of the position of the sulfate in T cell activation, the synthesis of three β-D-galactosylceramides, variously bearing a sulfate at position 2, 4, or 6 of galactose, has been planned and carried out. The compounds were synthesized by an or thogonal sulfation strategy from a common β-o-galactosylceramide scaffold, which was in turn obtained through an efficient glycosylation reaction between a fully orthogonally protected galactosyl imidate and 3-O-ben zoylazidosphingosine. Immunological evaluation of the three sulfated compounds in CD 1a-mediated T cell activation, in comparison with natural sulfatide, provided evidence of the influence of the sulfate position in the recognition event between the antigen, the CD1 protein and the T cell receptor.
KW - Carbohydrate scaffold
KW - Galactosylceramides
KW - Glycolipids
KW - Protecting groups
KW - Sulfatide
UR - http://www.scopus.com/inward/record.url?scp=33746271586&partnerID=8YFLogxK
U2 - 10.1002/chem.200501586
DO - 10.1002/chem.200501586
M3 - Article
SN - 0947-6539
VL - 12
SP - 5587
EP - 5595
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 21
ER -