CD1a protein binds sulfatide (3-O-sulfo-b-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 b-D-galactosylceramides, variously bearing a sulfate at position 2, 4, or 6 of galactose, has been planned and carried out. The compds. were synthesized by an orthogonal sulfation strategy from a common b-D-galactosylceramide scaffold, which was in turn obtained through an efficient glycosylation reaction between a fully orthogonally protected galactosyl imidate and 3-O-benzoylazidosphingosine. Immunol. evaluation of the three sulfated compds. in CD1a-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.
Synthesis of sulfated galactocerebrosides from an orthogonal b-D-galactosylceramide scaffold for the study of CD1-antigen interactions / F. Compostella, S. Ronchi, L. Panza, S. Mariotti, L. Mori, G. De Libero, F.C.V. Ronchetti. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 12:21(2006 Jul 17), pp. 5587-5595.
Synthesis of sulfated galactocerebrosides from an orthogonal b-D-galactosylceramide scaffold for the study of CD1-antigen interactions
F. CompostellaPrimo
;S. RonchiSecondo
;F.C.V. RonchettiUltimo
2006
Abstract
CD1a protein binds sulfatide (3-O-sulfo-b-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 b-D-galactosylceramides, variously bearing a sulfate at position 2, 4, or 6 of galactose, has been planned and carried out. The compds. were synthesized by an orthogonal sulfation strategy from a common b-D-galactosylceramide scaffold, which was in turn obtained through an efficient glycosylation reaction between a fully orthogonally protected galactosyl imidate and 3-O-benzoylazidosphingosine. Immunol. evaluation of the three sulfated compds. in CD1a-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.Pubblicazioni consigliate
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