4.5 Article

Design and Synthesis of Oligoamide-Based Double -Helix Mimetics

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 17, Pages 3433-3445

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300363

Keywords

Synthesis design; Amides; Peptidomimetics; Hydrogen bonds; Helical structures

Funding

  1. National Science Foundation (NSF) [CHE0750357]
  2. National Institutes of Health (NIH) [CA67771]
  3. University of Oxford, UK

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An extensive series of bis-oligobenzamides and bis-oligopyridylamides have been efficiently prepared and studied by X-ray analysis and computational methods. A modular synthesis led to double -helix mimics bearing between two and ten branched side-chains. The inter-helix angle and distance can be tuned by varying the length and rigidity of the spacer, thereby reproducing the recognition domains of a range of super-secondary structures.

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