Fluorinated pseudoprolines
Our group is interested in the preparation of trifluoromethylated pseudoprolines (CF3-ΨPro) as new proline substitutes. The introduction of a CF3 group leads to stable pseudoproline units since, unlike non-fluorinated pseudoproline units, they are not hydrolysable in an acid medium. Moreover, increased conformational constraints and specific properties related to the introduction of fluorine atoms have been demonstrated during their incorporation into a peptide chain. We are currently developing efficient peptide coupling methods for the formation of N- or C-terminal dipeptides incorporating CF3-ΨPro motifs.
- Selected publications
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1. Incorporation of Trifluoromethylated Proline and Surrogates into Peptides: Application to the Synthesis of Fluorinated Analogues of the Neuroprotective Glycine-Proline-Glutamate (GPE) Tripeptide. Simon, J.; Pytkowicz, J.; Lensen, N.; Chaume, G.; Brigaud, T. J. Org. Chem. 2016, 81, 5381-5392.
2.Incorporation of CF3−Pseudoprolines into Peptides: A Methodological Study, Chaume, G.; Simon, J.; Caupène, C.; Lensen, N.; Miclet, E.; Brigaud, T. J. Org. Chem. 2013, 78, 10144-10153.
3.Conformational properties of peptides incorporating a fluorinated pseudoproline residue, Chaume, G.; Feytens, D.; Chassaing, G.; Lavielle, S.; Brigaud, T.; Miclet, E. New J. Chem. 2013, 37, 1336-1342.
4.Local control of the cis-trans isomerization and backbone dihedral angles in peptides using trifluoromethylated pseudoprolines, Feytens, D.; Chaume, G.; Chassaing, G.; Lavielle, S.; Brigaud, T.; Byun, B. J.; Kang, Y. K.; Miclet, E. J. Phys. Chem. B 2012, 116, 4069-4079.
5.Synthesis of 2-Trifluoromethyl-1,3-oxazolidines as Hydrolytically Stable Pseudoprolines, Chaume, G. ; Barbeau, O. ; Lesot, P. ; Brigaud, T. J. Org. Chem. 2010, 75, 4135-4145.