title: Chiral dipeptide mimics possessing a fluoroolefin moiety: a relevant tool for conformational and medicinal studies.
abstract: The replacement of the amide bond in a peptide backbone is a promising strategy in peptidomimetic drug research. Over the various amide bond surrogates, the fluoroolefin moiety has been successfully developed as an effective mimic. Today, fluorine-containing compounds account for a large proportion of new active molecules in life sciences. The synthesis of fluoroolefin peptide mimics is not a trivial task and innovative approaches often need to be addressed, in particular for the stereocontrol of the double bond configuration and the chiral centres adjacent to the fluoroalkene. These fluorinated peptidomimetics have been synthesised and evaluated as metabolically stable and/or conformationally constrained analogs of enzyme inhibitors, and as tools for probing the function, structure, and binding process of receptors.
authors.affiliation: UMR CNRS 6014, ECOFH, IRCOF, INSA de Rouen, 1 rue Tesniere, F-76131, Mont-Saint-Aignan, France.
authors.forename: Samuel
authors.initials: S
authors.lastname: Couve-Bonnaire
authors.forename: Dominique
authors.initials: D
authors.lastname: Cahard
authors.forename: Xavier
authors.initials: X
authors.lastname: Pannecoucke
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D004151:Dipeptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D018716:Molecular Mimicry; D010920:Placenta / Q000201:enzymology; D011480:Protease Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011487:Protein Conformation; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D004151:Dipeptides; D011480:Protease Inhibitors