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Conception et synthèse de nouvelles classes d’iminosucres d’intérêt biologique : ingénierie click pour des systèmes multivalents

Abstract : Recent reports have demonstrated the first pieces of evidence of a strong multivalent effect in glycosidase inhibition by iminosugars, with affinity enhancements close to 10000. In order to understand the different parameters of this “cluster effect” and to continue its optimization, new scaffolds must be designed. The first research topic was thus to develop a set of « Click » Chemistry engineering techniques for the synthesis of multivalent systems, with the development of a Sweet LEGO® strategy. In the end, it would allow an easy access to a broad range of prefunctionalized neocyclodextrins. The second research topic consisted in a structure-activity relationship study by varying the molecular polyalkyne scaffold used for the preparation of new clusters by way of « Click » Chemistry. They allowed to investigate the specific features of the iminosugar cluster effect in the inhibition of glycosidases. In particular, a compound of unprecedented valency bearing 30 iminosugar units demonstrated an unprecedented dramatic affinity enhancement for the inhibition of a model enzyme (Jack bean alpha-mannosidase).
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Mathieu Lepage. Conception et synthèse de nouvelles classes d’iminosucres d’intérêt biologique : ingénierie click pour des systèmes multivalents. Autre. Université de Strasbourg, 2014. Français. ⟨NNT : 2014STRAF049⟩. ⟨tel-01647224⟩

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