ArticleNature chemistry2016
Oxadiazole grafts in peptide macrocycles.
Article in Nature chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 56 papers.
What it found
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
56 citing papers in PubMed.
- Bridging Heterocycle-Mediated Hydrogen Bonding Facilitates Permeability of Polar Macrobicycles.Journal of the American Chemical Society · 2026Article
- Frame-Shifted Synthesis of Oligoheterocycles as a Platform for Molecular Design.Angewandte Chemie (International ed. in English) · 2026Article
- Backbone Alterations in Cyclic Peptides Influence Both Membrane Permeability and Biological Activity.Journal of medicinal chemistry · 2025Article
- Chemoselective synthesis of 1,3,4-thiadiazoles from acyl hydrazines and nitroalkanes using elemental sulfur.Nature communications · 2025Article
- MultiCycPermea: accurate and interpretable prediction of cyclic peptide permeability using a multimodal image-sequence model.BMC biology · 2025Article
- Peptide Backbone Editing via Post-Translational O to C Acyl Shift.Journal of the American Chemical Society · 2025Article
- Chemoselective, regioselective, and positionally selective fluorogenic stapling of unprotected peptides for cellular uptake and direct cell imaging.Chemical science · 2025Article
- An Electrosynthesis of 1,3,4-Oxadiazoles from N-Acyl Hydrazones.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Recent Advances in Metal-Free Peptide Stapling Strategies.Chem & bio engineering · 2024Review
- CycPeptMP: enhancing membrane permeability prediction of cyclic peptides with multi-level molecular features and data augmentation.Briefings in bioinformatics · 2024Article
- Synthesis of Membrane-Permeable Macrocyclic Peptides via Imidazopyridinium Grafting.Journal of the American Chemical Society · 2024Article
- Photochemical three-component assembly of tri-substituted oxazoles through a carbenic phosphorus-nitrile hybrid ylide formation/trapping cascade.Chemical science · 2024Article
- Non-symmetric stapling of native peptides.Nature reviews. Chemistry · 2024Review
- Cell penetration of oxadiazole-containing macrocycles.RSC chemical biology · 2024Article
- Insights on Structure-Passive Permeability Relationship in Pyrrole and Furan-Containing Macrocycles.Journal of medicinal chemistry · 2024Article
- Applications of biaryl cyclization in the synthesis of cyclic enkephalin analogs with a highly restricted flexibility.Amino acids · 2024Article
- Diversifying DNA-Tagged Amines by Isocyanide Multicomponent Reactions for DNA-Encoded Library Synthesis.ACS omega · 2024Article
- Are peptidomimetics the compounds of choice for developing new modulators of the JAK-STAT pathway?Frontiers in immunology · 2024Review
- Expedient and divergent synthesis of unnatural peptides through cobalt-catalyzed diastereoselective umpolung hydrogenation.Science advances · 2023Article
- An amide to thioamide substitution improves the permeability and bioavailability of macrocyclic peptides.Nature communications · 2023Article
Corrections and comments
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Synthetic methods that provide control over macrocycle conformation and, at the same time, mitigate the polarity of peptide bonds represent valuable tools for the discovery of new bioactive molecules. Here, we report a macrocyclization reaction between a linear peptide, an aldehyde and (N-isocyanimino)triphenylphosphorane. This process generates head-to-tail cyclic peptidomimetics in a single step. This method is tolerant to variation in the peptide and aldehyde components and has been applied for the synthesis of 15-, 18-, 21- and 24-membered rings. The resulting peptide macrocycles feature a 1,3,4-oxadiazole and a tertiary amine in their scaffolds. This non-canonical backbone region acts as an endocyclic control element that promotes and stabilizes a unique intramolecular hydrogen-bond network and can lead to macrocycles with conformationally rigid turn structures. Oxadiazole-containing macrocycles can also display a high passive membrane permeability, an important property for the development of bioavailable peptide-based therapeutics.
Identifiers
27874866What OpenQuestion holds
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.