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Theses

Pseudopeptides à motif fluorooléfine : conception, synthèse, distérosélective et évaluation biologique et structurale

Abstract : Fluoroorganic compounds are increasingly popular owing to their wide range of biological applications. For example, in the field of medicinal chemistry, fluorinated molecules clearlyalter physicochemical properties compared to non-fluorinated derivatives, and often with animproved therapeutic profile.In this context, our laboratory is interested in the development of new fluoropeptidomimetics aiming at circumventing common problems associated with peptides(poor bioavaibility, flexibility). For this purpose, the fluoroolefin moiety (CF=CH) can act as aneffective peptide bond mimic due to steric and electronic similarities.In our project aiming at proposing general synthesis methods of fluorinated pseudopeptides featuring a fluoroolefin moiety as the peptide bond analogue, we develop a new strategy based on nucleophilic addition of organometallic reagents to chiral N-(tert-butanesulfinyl)-a-fluoroenimines. This methodology allows us to control the asymmetric center on the Nterminalside of the peptide.Then, we applied our strategy to the synthesis of biologically active compound such as the26RFa, a neuropeptide involved in regulation and food intake. In this context, several fluorinated dipeptides have been synthesized and incorporated into the natural heptapeptide for a structure-activity relationship study.
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Camille Pierry. Pseudopeptides à motif fluorooléfine : conception, synthèse, distérosélective et évaluation biologique et structurale. Autre. INSA de Rouen, 2010. Français. ⟨NNT : 2010ISAM0022⟩. ⟨tel-00559646⟩

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