Les exo-glycals activés pour la synthèse de dérivés saccharidiques complexes : application à la préparation de glycoamino acides et de peptidomimétiques

Abstract : This work is focused on the development of new synthetic pathways for exo-glycals functionalization and synthesis of bioactive compounds. The first part of this manuscript describes the efficient preparation of new tertiary S-glycosides and [gamma]-glycoamino acids via Michael addition of thiols derivatives and carbanions on anomeric carbon of exo-glycals. The obtained [gamma]-glycoamino acids were then incorporated in [alpha/gamma] mixed peptides and their structural properties were studied by NMR, IR, CD and molecular modelling studies. Furthermore, cyclic multivalent platforms were built by intramolecular cyclization of these entities. The second part of the manuscript concerns the elaboration of peptidomimetics targeting neuropilin-1 receptor, implicated in tumor angiogenesis. Based on molecular modeling studies, some compounds showed interesting binding affinity for NRP-1 receptor and one of them displayed promising properties toward inhibition of tubule formation
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Mylène Richard. Les exo-glycals activés pour la synthèse de dérivés saccharidiques complexes : application à la préparation de glycoamino acides et de peptidomimétiques. Autre. Université de Lorraine, 2015. Français. ⟨NNT : 2015LORR0133⟩. ⟨tel-01754621⟩

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