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Monofluoroalkene‐Isostere as a 19 F NMR Label for the Peptide Backbone: Synthesis and Evaluation in Membrane‐Bound PGLa and (KIGAKI) 3
Author(s) -
Drouin Myriam,
Wadhwani Parvesh,
Grage Stephan L.,
Bürck Jochen,
Reichert Johannes,
Tremblay Sébastien,
Mayer Marie Sabine,
Diel Christian,
Staub Alexander,
Paquin JeanFrançois,
Ulrich Anne S.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905054
Subject(s) - isostere , dipeptide , peptide , chemistry , antimicrobial peptides , stereochemistry , side chain , membrane , amino acid , nuclear magnetic resonance spectroscopy , helix (gastropod) , cyclic peptide , combinatorial chemistry , organic chemistry , biochemistry , biology , polymer , ecology , snail
Solid‐state 19 F NMR is a powerful method to study the interactions of biologically active peptides with membranes. So far, in labelled peptides, the 19 F‐reporter group has always been installed on the side chain of an amino acid. Given the fact that monofluoroalkenes are non‐hydrolyzable peptide bond mimics, we have synthesized a monofluoroalkene‐based dipeptide isostere, Val‐Ψ[( Z )‐CF=CH]‐Gly, and inserted it in the sequence of two well‐studied antimicrobial peptides: PGLa and (KIGAKI) 3 are representatives of an α‐helix and a β‐sheet. The conformations and biological activities of these labeled peptides were studied to assess the suitability of monofluoroalkenes for 19 F NMR structure analysis.