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Trifluoromethylated proline analogues as efficient tools to enhance the hydrophobicity and to promote passive diffusion transport of the l-prolyl-l-leucyl glycinamide (PLG) tripeptide†
Martin Oliver,Charlène Gadais,Júlia García-Pindado,Meritxell Teixidó,Nathalie Lensen,Grégory Chaume,Thierry Brigaud
RSC Advances Pub Date : 04/18/2018 00:00:00 , DOI:10.1039/C8RA02511H
Abstract

The synthesis of four CF3-proline analogues of the PLG peptide is reported. Our results show that the incorporation of trifluoromethylated amino acids (Tfm-AAs) at the N-terminal position of a peptide significantly increases its hydrophobicity. In addition, depending on the relative configuration and the position of the CF3 group, Tfm-AAs can also promote passive diffusion transport.

Graphical abstract: Trifluoromethylated proline analogues as efficient tools to enhance the hydrophobicity and to promote passive diffusion transport of the l-prolyl-l-leucyl glycinamide (PLG) tripeptide
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