ArticleJournal of the American Chemical Society2016
Impact of γ-Amino Acid Residue Preorganization on α/γ-Peptide Foldamer Helicity in Aqueous Solution.
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 10 papers.
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Who cites it
10 citing papers in PubMed, 48 citations in OpenAlex.
- Synthesis and Characterization of a Two-Station Two-Gate Calix[6]arene-Based [2]Catenane.Molecules (Basel, Switzerland) · 2025Article
- Foldamers controlled by functional triamino acids: structural investigation of α/γ-hybrid oligopeptides.Communications chemistry · 2024Article
- Synthesis of a glycan hairpin.Nature chemistry · 2023Article
- Crystal Structure and NMR of an α,δ-Peptide Foldamer Helix Shows Side-Chains are Well Placed for Bifunctional Catalysis: Application as a Minimalist Aldolase Mimic.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2023Article
- Crystal Structure and NMR of an α,δ-Peptide Foldamer Helix Shows Side-Chains are Well Placed for Bifunctional Catalysis: Application as a Minimalist Aldolase Mimic.Angewandte Chemie (International ed. in English) · 2023Article
- Lights and Shadows on the Therapeutic Use of Antimicrobial Peptides.Molecules (Basel, Switzerland) · 2022Review
- Synthetic approaches to metal-coordination-directed macrocyclic complexes.Frontiers in chemistry · 2022Review
- Assignment of Vibrational Circular Dichroism Cross-Referenced Electronic Circular Dichroism Spectra of Flexible Foldamer Building Blocks: Towards Assigning Pure Chiroptical Properties of Foldamers.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Solid-Phase Synthesis and Circular Dichroism Study of β-ABpeptoids.Molecules (Basel, Switzerland) · 2019Article
- Library Design-Facilitated High-Throughput Sequencing of Synthetic Peptide Libraries.ACS combinatorial science · 2017Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
α/γ-Peptide foldamers containing either γ(4)-amino acid residues or ring-constrained γ-amino acid residues have been reported to adopt 12-helical secondary structure in nonpolar solvents and in the solid state. These observations have engendered speculation that the seemingly flexible γ(4) residues have a high intrinsic helical propensity and that residue-based preorganization may not significantly stabilize the 12-helical conformation. However, the prior studies were conducted in environments that favor intramolecular H-bond formation. Here, we use 2D-NMR to compare the ability of γ(4) residues and cyclic γ residues to support 12-helix formation in more challenging environments, methanol and water. Both γ residue types support 12-helical folding in methanol, but only the cyclically constrained γ residues promote helicity in water. These results demonstrate the importance of residue-based preorganization strategies for achieving stable folding among short foldamers in aqueous solution.
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