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Fluorinated Pseudopeptide Analogues of the Neuropeptide 26RFa: Synthesis, Biological, and Structural Studies
Author(s) -
Pierry Camille,
CouveBonnaire Samuel,
Guilhaudis Laure,
Neveu Cindy,
Marotte Amélie,
Lefranc Benjamin,
Cahard Dominique,
SégalasMilazzo Isabelle,
Leprince Jérôme,
Pannecoucke Xavier
Publication year - 2013
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201300325
Subject(s) - moiety , dipeptide , chemistry , olefin fiber , peptide , stereochemistry , neuropeptide , combinatorial chemistry , metabolic stability , biochemistry , in vitro , receptor , catalysis
A series of four fluorinated dipeptide analogues each containing a fluoro‐olefin moiety as peptide bond surrogate has been designed and synthesized. These motifs have been successfully introduced into the bioactive C‐terminal heptapeptide of the neuropeptide 26RFa by conventional SPPS. We then evaluated the ability of the generated pseudopeptides to increase [Ca 2+ ] i in GPR103‐transfected cells. For these fluorinated analogues, greater stability in human serum was observed. Their conformations were also investigated, leading to the valuable identification of differences depending on the position of the fluoro‐olefin moiety in the sequence.