Synthesis of sulfated galactocerebrosides from an orthogonal β-D-galactosylceramide scaffold for the study of CD1-antigen interactions

Federica Compostella, Silvia Ronchi, Luigi Panza, Sabrina Mariotti, Lucia Mori, Gennaro De Libero, Fiamma Ronchetti

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

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.

Lingua originaleInglese
pagine (da-a)5587-5595
Numero di pagine9
RivistaChemistry - A European Journal
Volume12
Numero di pubblicazione21
DOI
Stato di pubblicazionePubblicato - 17 lug 2006

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