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Stereoselective synthesis and immunogenic activity of the C-analogue of sulfatide |
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| Authors: | Modica Emilia Compostella Federica Colombo Diego Franchini Laura Cavallari Marco Mori Lucia De Libero Gennaro Panza Luigi Ronchetti Fiamma |
| Affiliation: | Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Via Saldini 50, 20133-Milano, Italy, and Experimental Immunology, Department of Research, Basel University Hospital, Hebelstrasse 20, 4031-Basel, Switzerland. |
| Abstract: | [Structure: see text] The C-sulfatide 1b was synthesized through a [2,3]-Wittig sigmatropic rearrangement and a Horner-Wadsworth-Emmons olefination as the key steps. The C-analogue 1b is less immunogenic than natural sulfatide 1a, but induces a preferential secretion of the proinflammatory cytokine IFN-gamma. |
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