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Synthèse d’α-C-galactosylcéramides difluorés et évaluation de leurs propriétés immunorégulatrices pour le traitement des maladies autoimmunes systémiques

Abstract : O-glycoconjugates and carbohydrate-based molecules are natural compounds implied in many biological processes. However, their properties are burdened by the low in vivo stability of the osidic bond. It is thus interesting to develop non hydrolizable mimetics. We were interested in the replacement of the anomeric oxygen by a gem-difluoromethylene group.The synthesis of difluorinated α-galactosylceramides featuring various lipidic chain lenghts is described herein. The C-glycosidic part of these molecules is construted by a sequence of radical addition and diastereoselective reduction. The phytosphingosine chain is introduced on this intermediate by an O-2 to C-1' migration and the ceramide synthesis is completed by a petidic coupling. Four analogues featuring various phytosphingosines chains (C₅H₁₁, C₂₄H₄₉) and fatty acids (C₇H₁₅, C₁₅H₃₁ et C₂₅H₅₁) were synthetized and biologically assessed.
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Sophie Colombel. Synthèse d’α-C-galactosylcéramides difluorés et évaluation de leurs propriétés immunorégulatrices pour le traitement des maladies autoimmunes systémiques. Autre. INSA de Rouen, 2012. Français. ⟨NNT : 2012ISAM0014⟩. ⟨tel-00776792⟩

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