Synthesis of Sulfated Galactocerebrosides from an Orthogonal β-D-Galactosylceramide Scaffold for the Study of CD1–Antigen Interactions
✍ Scribed by Federica Compostella; Silvia Ronchi; Luigi Panza; Sabrina Mariotti; Lucia Mori; Gennaro De Libero; Fiamma Ronchetti
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- English
- Weight
- 184 KB
- Volume
- 12
- Category
- Article
- ISSN
- 0947-6539
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✦ Synopsis
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 orthogonal sulfation strategy from a common β‐D‐galactosylceramide scaffold, which was in turn obtained through an efficient glycosylation reaction between a fully orthogonally protected galactosyl imidate and 3‐O‐benzoylazidosphingosine. Immunological evaluation of the three sulfated compounds 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.