Consequences of Isostructural Main‐Chain Modifications for the Design of Antimicrobial Foldamers: Helical Mimics of Host‐Defense Peptides Based on a Heterogeneous Amide/Urea Backbone

Isosteric Substitutions of Urea to Thiourea and Selenourea in Aliphatic Oligourea Foldamers: Site‐Specific Perturbation of the Helix Geometry

“…By allowing helix parameters (geometry and polarity) to be tuned with precision, a positional thiourea scan may prove useful to study the interplay between folding, membrane interacting properties, and antibacterial activities of oligoureas mimicking host defense peptides. [43] The facile transformation of thioureas into guanidiniums [44] and the importance of this moiety in biology, medicinal chemistry, drug delivery, and supramolecular structures also suggests application of (thio)urea hybrid oligomers as synthetic intermediates towards the elaboration of oligomers incorporating N,N'-linked guanidinium units at selected positions in the main chain. [45] The synthesis, and exploration of the folding and chemical properties of these novel urea/guanidinium hybrid backbones will be reported in due course.…”

17 The protein epitope mimetic approach to protein-protein interaction inhibitors

“…Aromatic and aliphatic N,N'-linked oligoureas have also been designed to fold and/or self-assemble in a controlled manner (Fischer and Guichard 2010). The development of foldamers with heterogeneous backbones formed by combining multiple residue types (mixed α/ß-peptides, oligo-urea/amides) has also been reported (Claudon et al 2010;.…”

Structural analysis of two foldamer-type oligoamides – the effect of hydrogen bonding on solvate formation, crystal structures and molecular conformation

“…Lettering used in the NMR assignment. Assigned 1 H and 13 C spectra and 2D COSY, HMBC and HMQC spectra of compounds 2 and 3. 1 H and 13 C spectra of compound 1.…”

“…Assigned 1 H and 13 C spectra and 2D COSY, HMBC and HMQC spectra of compounds 2 and 3. 1 H and 13 C spectra of compound 1. NOESY spectra of compound 45 3 in THF-d 8 and acetone-d 6 .…”