ArticleChembiochem : a European journal of chemical biology2015
Ribosomal Synthesis of Natural-Product-Like Bicyclic Peptides in Escherichia coli.
Article in Chembiochem : a European journal of chemical biology, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 39 citations in OpenAlex.
- Article
- Genetic Code Expansion: Recent Developments and Emerging Applications.Chemical reviews · 2025Review
- A Strategy to Select Macrocyclic Peptides Featuring Asymmetric Molecular Scaffolds as Cyclization Units by Phage Display.Journal of the American Chemical Society · 2022Article
- MOrPH-PhD: A Phage Display System for the Functional Selection of Genetically Encoded Macrocyclic Peptides.Methods in molecular biology (Clifton, N.J.) · 2022Article
- The Discovery of Peptide Macrocycle Rescuers of Pathogenic Protein Misfolding and Aggregation by Integrating SICLOPPS Technology and Ultrahigh-Throughput Screening in Bacteria.Methods in molecular biology (Clifton, N.J.) · 2022Article
- Biosynthetic Strategies for Macrocyclic Peptides.Molecules (Basel, Switzerland) · 2021Review
- Small and Simple, yet Sturdy: Conformationally Constrained Peptides with Remarkable Properties.International journal of molecular sciences · 2021Review
- Rationally Designed Bicyclic Peptides Prevent the Conversion of Aβ42 Assemblies Into Fibrillar Structures.Frontiers in neuroscience · 2021Article
- Expanding the Chemical Diversity of Genetically Encoded Libraries.ACS combinatorial science · 2020Article
- A rationally designed bicyclic peptide remodels Aβ42 aggregation in vitro and reduces its toxicity in a worm model of Alzheimer's disease.Scientific reports · 2020Article
- Expanded toolbox for directing the biosynthesis of macrocyclic peptides in bacterial cells.Chemical science · 2020Article
- Direct, Competitive Comparison of Linear, Monocyclic, and Bicyclic Libraries Using mRNA Display.ACS combinatorial science · 2020Article
- MOrPH-PhD: An Integrated Phage Display Platform for the Discovery of Functional Genetically Encoded Peptide Macrocycles.ACS central science · 2020Article
- Bacterial production and direct functional screening of expanded molecular libraries for discovering inhibitors of protein aggregation.Science advances · 2019Article
- Selection, Addiction and Catalysis: Emerging Trends for the Incorporation of Noncanonical Amino Acids into Peptides and Proteins in Vivo.Chembiochem : a European journal of chemical biology · 2019Review
- Review
- Enzyme stabilization via computationally guided protein stapling.Proceedings of the National Academy of Sciences of the United States of America · 2017Article
- Bicyclic Peptides as Next-Generation Therapeutics.Chemistry (Weinheim an der Bergstrasse, Germany) · 2017Review
- Design and Evolution of a Macrocyclic Peptide Inhibitor of the Sonic Hedgehog/Patched Interaction.Journal of the American Chemical Society · 2017Article
- Highly Constrained Bicyclic Scaffolds for the Discovery of Protease-Stable Peptides via mRNA Display.ACS chemical biology · 2017Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Methods to access natural-product-like macrocyclic peptides can disclose new opportunities for the exploration of this important structural class for chemical biology and drug discovery applications. Here, the scope and mechanism of a novel strategy for directing the biosynthesis of thioether-bridged bicyclic peptides in bacterial cells was investigated. This method entails split intein-catalyzed head-to-tail cyclization of a ribosomally produced precursor peptide, combined with inter-side-chain crosslinking through a genetically encoded cysteine-reactive amino acid. This strategy could be successfully applied to achieve formation of structurally diverse bicyclic peptides with high efficiency and selectivity in Escherichia coli. Insights into the sequence of reactions underlying the peptide bicyclization process were gained from time-course experiments. Finally, the potential utility of this methodology toward the discovery of macrocyclic peptides with enhanced functional properties was demonstrated through the isolation of a bicyclic peptide with sub-micromolar affinity for streptavidin.
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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.