Stabilising Peptoid Helices Using Non‐Chiral Fluoroalkyl Monomers
| Autor: | Steven L. Cobb, Diana Gimenez, Juan A. Aguilar, Elizabeth H. C. Bromley |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Protein Conformation
alpha-Helical Magnetic Resonance Spectroscopy Peptidomimetic Chemical biology Crystallography X-Ray 010402 general chemistry 01 natural sciences Catalysis Peptoids chemistry.chemical_compound NMR spectroscopy Amide Protein secondary structure 010405 organic chemistry Circular Dichroism Communication Stereoisomerism secondary structure Peptoid Fluorine General Chemistry Nuclear magnetic resonance spectroscopy General Medicine Amides Combinatorial chemistry Communications 0104 chemical sciences 3. Good health Kinetics Monomer chemistry Peptidomimetics Chirality (chemistry) |
| Zdroj: | Angewandte chemie international edition, 2018, Vol.57(33), pp.10549-10553 [Peer Reviewed Journal] Angewandte Chemie (International Ed. in English) |
| ISSN: | 1521-3757 0044-8249 |
| Popis: | Stability towards protease degradation combined with modular synthesis has made peptoids of considerable interest in the fields of chemical biology, medicine, and biomaterials. Given their tertiary amide backbone, peptoids lack the capacity to hydrogen‐bond, and as such, controlling secondary structure can be challenging. The incorporation of bulky, charged, or chiral aromatic monomers can be used to control conformation but such building blocks limit applications in many areas. Through NMR and X‐ray analysis we demonstrate that non‐chiral neutral fluoroalkyl monomers can be used to influence the Kcis/trans equilibria of peptoid amide bonds in model systems. The cis‐isomer preference displayed is highly unprecedented given that neither chirality nor charge is used to control the peptoid amide conformation. The application of our fluoroalkyl monomers in the design of a series of linear peptoid oligomers that exhibit stable helical structures is also reported. |
| Databáze: | OpenAIRE |
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