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

The synthesis of four CF(3)-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...

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Autores principales: Oliver, Martin, Gadais, Charlène, García-Pindado, Júlia, Teixidó, Meritxell, Lensen, Nathalie, Chaume, Grégory, Brigaud, Thierry
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9079923/
https://www.ncbi.nlm.nih.gov/pubmed/35540789
http://dx.doi.org/10.1039/c8ra02511h
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author Oliver, Martin
Gadais, Charlène
García-Pindado, Júlia
Teixidó, Meritxell
Lensen, Nathalie
Chaume, Grégory
Brigaud, Thierry
author_facet Oliver, Martin
Gadais, Charlène
García-Pindado, Júlia
Teixidó, Meritxell
Lensen, Nathalie
Chaume, Grégory
Brigaud, Thierry
author_sort Oliver, Martin
collection PubMed
description The synthesis of four CF(3)-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 CF(3) group, Tfm-AAs can also promote passive diffusion transport.
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spelling pubmed-90799232022-05-09 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 Oliver, Martin Gadais, Charlène García-Pindado, Júlia Teixidó, Meritxell Lensen, Nathalie Chaume, Grégory Brigaud, Thierry RSC Adv Chemistry The synthesis of four CF(3)-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 CF(3) group, Tfm-AAs can also promote passive diffusion transport. The Royal Society of Chemistry 2018-04-18 /pmc/articles/PMC9079923/ /pubmed/35540789 http://dx.doi.org/10.1039/c8ra02511h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Oliver, Martin
Gadais, Charlène
García-Pindado, Júlia
Teixidó, Meritxell
Lensen, Nathalie
Chaume, Grégory
Brigaud, Thierry
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9079923/
https://www.ncbi.nlm.nih.gov/pubmed/35540789
http://dx.doi.org/10.1039/c8ra02511h
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