ArticleJournal of the American Chemical Society2016
Length-Dependent Formation of Transmembrane Pores by 310-Helical α-Aminoisobutyric Acid Foldamers.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Innovative Self-Assembly of 15-Mer Chimeric α-Peptide-Oligourea Foldamers toward ClSmall science · 2024Article
- An Exceptionally Active and Highly Selective Perchlorate Transporter Containing a Trimesic Amide Scaffold.Molecules (Basel, Switzerland) · 2024Article
- Unnatural helical peptidic foldamers as protein segment mimics.Chemical Society reviews · 2023Review
- Screw sense and screw sensibility: communicating information by conformational switching in helical oligomers.Chemical Society reviews · 2023Review
- Dissecting Solvent Effects on Hydrogen Bonding.Angewandte Chemie (International ed. in English) · 2022Article
- An Orthogonal Dynamic Covalent Chemistry Tool for Ring-Opening Polymerization of Cyclic Oligochalcogenides on Detachable Helical Peptide Templates.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- The folding propensity of α/sulfono-γ-AA peptidic foldamers with both left- and right-handedness.Communications chemistry · 2021Article
- Insight into the Mechanism of Action and Peptide-Membrane Interactions of Aib-Rich Peptides: Multitechnique Experimental and Theoretical Analysis.Chembiochem : a European journal of chemical biology · 2021Article
- Transmembrane Ion Channels Formed by a Star of David [2]Catenane and a Molecular Pentafoil Knot.Journal of the American Chemical Society · 2020Article
- Switchable foldamer ion channels with antibacterial activity.Chemical science · 2020Article
- α-Helix-Mimicking Sulfono-γ-AApeptide Inhibitors for p53-MDM2/MDMX Protein-Protein Interactions.Journal of medicinal chemistry · 2020Article
- Inhibition of β-catenin/B cell lymphoma 9 protein-protein interaction using α-helix-mimicking sulfono-γ-AApeptide inhibitors.Proceedings of the National Academy of Sciences of the United States of America · 2019Article
- Braiding, branching and chiral amplification of nanofibres in supramolecular gels.Nature chemistry · 2019Article
- De Novo Left-Handed Synthetic Peptidomimetic Foldamers.Angewandte Chemie (International ed. in English) · 2018Article
- A spin-1 representation for dual-funnel energy landscapes.The Journal of chemical physics · 2018Article
- Homochirality of β-Peptides: A Significant Biomimetic Property of Unnatural Systems.ChemistryOpen · 2017Article
- Right-Handed Helical Foldamers Consisting of De Novo d-AApeptides.Journal of the American Chemical Society · 2017Article
- An α-Helix-Mimicking 12,13-Helix: Designed α/β/γ-Foldamers as Selective Inhibitors of Protein-Protein Interactions.Angewandte Chemie (International ed. in English) · 2016Article
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11 authors.
Funding
Abstract
The synthetic biology toolbox lacks extendable and conformationally controllable yet easy-to-synthesize building blocks that are long enough to span membranes. To meet this need, an iterative synthesis of α-aminoisobutyric acid (Aib) oligomers was used to create a library of homologous rigid-rod 310-helical foldamers, which have incrementally increasing lengths and functionalizable N- and C-termini. This library was used to probe the inter-relationship of foldamer length, self-association strength, and ionophoric ability, which is poorly understood. Although foldamer self-association in nonpolar chloroform increased with length, with a ∼ 14-fold increase in dimerization constant from Aib6 to Aib11, ionophoric activity in bilayers showed a stronger length dependence, with the observed rate constant for Aib11 ∼ 70-fold greater than that of Aib6. The strongest ionophoric activity was observed for foldamers with >10 Aib residues, which have end-to-end distances greater than the hydrophobic width of the bilayers used (∼ 2.8 nm); X-ray crystallography showed that Aib11 is 2.93 nm long. These studies suggest that being long enough to span the membrane is more important for good ionophoric activity than strong self-association in the bilayer. Planar bilayer conductance measurements showed that Aib11 and Aib13, but not Aib7, could form pores. This pore-forming behavior is strong evidence that Aibm (m ≥ 10) building blocks can span bilayers.
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