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- Title
Monofluoroalkene‐Isostere as a <sup>19</sup>F NMR Label for the Peptide Backbone: Synthesis and Evaluation in Membrane‐Bound PGLa and (KIGAKI)<sub>3</sub>.
- Authors
Drouin, Myriam; Wadhwani, Parvesh; Grage, Stephan L.; Bürck, Jochen; Reichert, Johannes; Tremblay, Sébastien; Mayer, Marie Sabine; Diel, Christian; Staub, Alexander; Paquin, Jean‐François; Ulrich, Anne S.
- Abstract
Solid‐state 19F NMR is a powerful method to study the interactions of biologically active peptides with membranes. So far, in labelled peptides, the 19F‐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 19F NMR structure analysis.
- Subjects
PEPTIDE synthesis; PEPTIDE antibiotics; PEPTIDE bonds; AMINO acids; PEPTIDES; LABELS
- Publication
Chemistry - A European Journal, 2020, Vol 26, Issue 7, p1511
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201905054