Compostella Federica, Ronchi Silvia, Panza Luigi, Mariotti Sabrina, Mori Lucia, De Libero Gennaro, Ronchetti Fiamma
Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Via Saldini 50, 20133-Milan, Italy.
Chemistry. 2006 Jul 17;12(21):5587-95. doi: 10.1002/chem.200501586.
CD1a protein binds sulfatide (3-O-sulfo-beta-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 beta-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 beta-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.
CD1a蛋白与硫苷脂（3 - O - 磺基 - β - D - 半乳糖基神经酰胺）结合形成抗原复合物，该复合物与T细胞受体相互作用并激活T细胞。为了评估硫酸根基团位置在T细胞活化中的作用，已设计并合成了三种β - D - 半乳糖基神经酰胺，它们在半乳糖的2、4或6位分别带有硫酸根。这些化合物通过正交硫酸化策略从共同的β - D - 半乳糖基神经酰胺支架合成，该支架又是通过完全正交保护的半乳糖基亚氨酸酯与3 - O - 苯甲酰叠氮鞘氨醇之间的高效糖基化反应获得的。与天然硫苷脂相比，对这三种硫酸化化合物在CD1a介导的T细胞活化中的免疫评估，提供了硫酸根基团位置对抗原、CD1蛋白和T细胞受体之间识别事件影响的证据。
