ArticleScience (New York, N.Y.)2019
Foldamer-templated catalysis of macrocycle formation.
Article in Science (New York, N.Y.), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 43 papers.
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Who cites it
43 citing papers in PubMed.
- Sequence-Dependent Folding of Recognition-Encoded Melamine Oligomers.Journal of the American Chemical Society · 2026Article
- Stereoselective Synthesis of Topologically Chiral Knots and Links: Synthesis and Applications.Molecules (Basel, Switzerland) · 2026Review
- Spatial Assembly of Mechanically Planar Chiral Rotaxanes on Rationally Designed Cavitands.Angewandte Chemie (International ed. in English) · 2025Article
- Mechanisms of Chiral Induction to Foldamer Backbones.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Site-selective protein editing by backbone extension acyl rearrangements.Nature chemical biology · 2025Article
- Bifunctional Catalysis of Aldol Reactions by Foldamer Dihydrazides: Assessment of Conformational Preorganization.Journal of the American Chemical Society · 2025Article
- A glycan foldamer that uses carbohydrate-aromatic interactions to perform catalysis.Nature chemistry · 2025Article
- Covalent Template-Directed Synthesis: A Powerful Tool for the Construction of Complex Molecules.Chemical reviews · 2025Review
- Dual Activation Modes Enable Bifunctional Catalysis of Aldol Reactions by Flexible Dihydrazides.Journal of the American Chemical Society · 2025Article
- Light-Mediated Interconversion between a Foldamer and a Self-Replicator.Journal of the American Chemical Society · 2024Article
- Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis.Chemical reviews · 2024Review
- Revealing the Effect of Stereocontrol on Intermolecular Interactions between Abiotic, Sequence-Defined Polyurethanes and a Ligand.ACS biomaterials science & engineering · 2024Article
- Complete Computational Reaction Mechanism for Foldamer-Catalyzed Aldol Condensation.ACS catalysis · 2024Article
- Scalable Synthesis of All Stereoisomers of 2-Aminocyclopentanecarboxylic Acid─A Toolbox for Peptide Foldamer Chemistry.The Journal of organic chemistry · 2024Article
- Nonthreaded Isomers of Sungsanpin and Ulleungdin Lasso Peptides Inhibit H1299 Cancer Cell Migration.ACS chemical biology · 2024Article
- Article
- 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
- Unnatural helical peptidic foldamers as protein segment mimics.Chemical Society reviews · 2023Review
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Authors and funding
4 authors.
Funding
Abstract
Macrocycles, compounds containing a ring of 12 or more atoms, find use in human medicine, fragrances, and biological ion sensing. The efficient preparation of macrocycles is a fundamental challenge in synthetic organic chemistry because the high entropic cost of large-ring closure allows undesired intermolecular reactions to compete. Here, we present a bioinspired strategy for macrocycle formation through carbon-carbon bond formation. The process relies on a catalytic oligomer containing α- and β-amino acid residues to template the ring-closing process. The α/β-peptide foldamer adopts a helical conformation that displays a catalytic primary amine-secondary amine diad in a specific three-dimensional arrangement. This catalyst promotes aldol reactions that form rings containing 14 to 22 atoms. Utility is demonstrated in the synthesis of the natural product robustol.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.