Condensation Approach to Aliphatic Oligourea Foldamers: Helices with N-(Pyrrolidin-2-ylmethyl)ureido Junctions

Condensation Approach to Aliphatic Oligourea Foldamers: Helices with N-(Pyrrolidin-2-ylmethyl)ureido Junctions

Caught in a fold: A simple and efficient coupling strategy to make aliphatic oligourea foldamers is reported. Crystal structures show that the pyrrolidine units (red; see picture) do not impair the 2.5‐helical folding of the oligoureas. This modular strategy enables assembly of long helical segments...

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Veröffentlicht in:Angewandte Chemie International Edition 2011-11, Vol.50 (48), p.11382-11385
Hauptverfasser: Fremaux, Juliette, Fischer, Lucile, Arbogast, Thomas, Kauffmann, Brice, Guichard, Gilles
Format: Artikel
Sprache:eng
Schlagworte:
Circular Dichroism
helical structures
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Conformation
Molecular Structure
peptidomimetics
Peptidomimetics - chemical synthesis
Peptidomimetics - chemistry
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
synthetic methods
urea
Urea - analogs & derivatives
Urea - chemical synthesis
Urea - chemistry
X-Ray Diffraction
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Zusammenfassung:Caught in a fold: A simple and efficient coupling strategy to make aliphatic oligourea foldamers is reported. Crystal structures show that the pyrrolidine units (red; see picture) do not impair the 2.5‐helical folding of the oligoureas. This modular strategy enables assembly of long helical segments containing non‐adjacent pyrrolidine units as exemplified by the synthesis of a helix that is approximately 40 Å long.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201105416