Aromatic Foldamer Helices as α‐Helix Extended Surface Mimetics. Issue 72 (30th November 2020)

• Record Type: Journal Article
• Authors: Zwillinger, Márton; Reddy, Post Sai; Wicher, Barbara; Mandal, Pradeep K.; Csékei, Márton; Fischer, Lucile; Kotschy, András; Huc, Ivan
• Is Part Of: Chemistry. Volume 26:Issue 72(2020)
• Page Start: 17366
• Page End: 17370
• Publication Date: 2020-11-30
• Subjects: aromatic foldamers -- peptidomimetics -- structure based design -- structure elucidation -- α-helix; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202004064
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Helically folded aromatic oligoamide foldamers have a size and geometrical parameters very distinct from those of α‐helices and are not obvious candidates for α‐helix mimicry. Nevertheless, they offer multiple sites for attaching side chains. It was found that some arrays of side chains at the surface of an aromatic helix make it possible to mimic extended α‐helical surfaces. Synthetic methods were developed to produce quinoline monomers suitably functionalized for solid phase synthesis. A dodecamer was prepared. Its crystal structure validated the initial design and showed helix bundling involving the α‐helix‐like interface. These results open up new uses of aromatic helices to recognize protein surfaces and to program helix bundling in water. Abstract : Different yet alike : Aromatic helices may be designed to display side chain patterns mimicking the surface of an extended α‐helix despite the considerable differences between the geometrical parameters of their backbones.