Incorporation of CF 3 -pseudoprolines into polyproline type II foldamers confers promising biophysical features.

Autor: Cayrou C; CY Cergy Paris Université, CNRS, BioCIS UMR 8076, 95000 Cergy Pontoise, France. simon.gonzalez1@cyu.fr.; Université Paris-Saclay, CNRS, BioCIS UMR 8076, 91400 Orsay, France., Walrant A; Laboratoire des Biomolécules, Sorbonne Université, École Normale Supérieure, PSL University, CNRS, LBM, 75005 Paris, France., Ravault D; Laboratoire des Biomolécules, Sorbonne Université, École Normale Supérieure, PSL University, CNRS, LBM, 75005 Paris, France., Guitot K; CY Cergy Paris Université, CNRS, BioCIS UMR 8076, 95000 Cergy Pontoise, France. simon.gonzalez1@cyu.fr.; Université Paris-Saclay, CNRS, BioCIS UMR 8076, 91400 Orsay, France., Noinville S; Laboratoire des Biomolécules, Sorbonne Université, École Normale Supérieure, PSL University, CNRS, LBM, 75005 Paris, France., Sagan S; Laboratoire des Biomolécules, Sorbonne Université, École Normale Supérieure, PSL University, CNRS, LBM, 75005 Paris, France., Brigaud T; CY Cergy Paris Université, CNRS, BioCIS UMR 8076, 95000 Cergy Pontoise, France. simon.gonzalez1@cyu.fr.; Université Paris-Saclay, CNRS, BioCIS UMR 8076, 91400 Orsay, France., Gonzalez S; CY Cergy Paris Université, CNRS, BioCIS UMR 8076, 95000 Cergy Pontoise, France. simon.gonzalez1@cyu.fr.; Université Paris-Saclay, CNRS, BioCIS UMR 8076, 91400 Orsay, France., Ongeri S; Université Paris-Saclay, CNRS, BioCIS UMR 8076, 91400 Orsay, France., Chaume G; CY Cergy Paris Université, CNRS, BioCIS UMR 8076, 95000 Cergy Pontoise, France. simon.gonzalez1@cyu.fr.; Université Paris-Saclay, CNRS, BioCIS UMR 8076, 91400 Orsay, France.
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2024 Aug 09; Vol. 60 (65), pp. 8609-8612. Date of Electronic Publication: 2024 Aug 09.
DOI: 10.1039/d4cc02895c
Abstrakt: The development and the use of fluorinated polyproline-type II (PPII) foldamers are still underexplored. Herein, trifluoromethyl pseudoprolines have been incorporated into polyproline backbones without affecting their PPII helicity. The ability of the trifluoromethyl groups to increase hydrophobicity and to act as 19 F NMR probes is demonstrated. Moreover, the enzymatic stability and the non-cytotoxicity of these fluorinated foldamers make them valuable templates for use in medicinal chemistry.
Databáze: MEDLINE
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