ArticleAngewandte Chemie (International ed. in English)2015
Acetone-Linked Peptides: A Convergent Approach for Peptide Macrocyclization and Labeling.
Article in Angewandte Chemie (International ed. in English), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 59 papers.
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Who cites it
59 citing papers in PubMed.
- Tetrazine-Enabled Peptide Macrocyclization and Bioorthogonal Cell Penetration Profiling.JACS Au · 2026Article
- Site-specific labelling of native peptides and proteins: chemical and enzymatic strategies.Beilstein journal of organic chemistry · 2026Review
- Cys-Lys stapling for unprotected peptides via tunable linkers.National science review · 2025Article
- Diverse thioether macrocyclized peptides through a radical SAM maturase.Proceedings of the National Academy of Sciences of the United States of America · 2025Article
- Intrastrand Peptide Staples That Promote β-Sheet Folding, Self-Assembly, and Amyloid Seeding.Journal of the American Chemical Society · 2025Article
- Highly Efficient Transpeptidase-Catalyzed Isopeptide Ligation.Journal of the American Chemical Society · 2025Article
- Late-Stage Reshaping of Phage-Displayed Libraries to Macrocyclic and Bicyclic Landscapes using a Multipurpose Linchpin.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
- Tackling Undruggable Targets with Designer Peptidomimetics and Synthetic Biologics.Chemical reviews · 2024Review
- Facile Peptide Macrocyclization and Multifunctionalization via Cyclen Installation.Small methods · 2024Article
- Site-Selective Antibody Conjugation with Dibromopyrazines.Bioconjugate chemistry · 2024Article
- Enhancing the Intrinsic Antiplasmodial Activity and Improving the Stability and Selectivity of a Tunable Peptide Scaffold Derived from Human Platelet Factor 4.ACS infectious diseases · 2024Article
- Diversification of Phage-Displayed Peptide Libraries with Noncanonical Amino Acid Mutagenesis and Chemical Modification.Chemical reviews · 2024Review
- An efficient mRNA display protocol yields potent bicyclic peptide inhibitors for FGFR3c: outperforming linear and monocyclic formats in affinity and stability.Chemical science · 2024Article
- An Update on Protein Kinases as Therapeutic Targets-Part II: Peptides as Allosteric Protein Kinase C Modulators Targeting Protein-Protein Interactions.International journal of molecular sciences · 2023Review
- Screening and optimization of phage display cyclic peptides against the WDR5 WBM site.RSC medicinal chemistry · 2023Article
- Identification of macrocyclic peptides which activate bacterial cylindrical proteases.RSC medicinal chemistry · 2023Article
- Biocompatible and Selective Generation of Bicyclic Peptides.Angewandte Chemie (International ed. in English) · 2022Article
- Lysine-Targeted Reversible Covalent Ligand Discovery for Proteins via Phage Display.Journal of the American Chemical Society · 2022Article
- Perfluoroaryl and Perfluoroheteroaryl Reagents as Emerging New Tools for Peptide Synthesis, Modification and Bioconjugation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
Macrocyclization is a broadly applied approach for overcoming the intrinsically disordered nature of linear peptides. Herein, it is shown that dichloroacetone (DCA) enhances helical secondary structures when introduced between peptide nucleophiles, such as thiols, to yield an acetone-linked bridge (ACE). Aside from stabilizing helical structures, the ketone moiety embedded in the linker can be modified with diverse molecular tags by oxime ligation. Insights into the structure of the tether were obtained through co-crystallization of a constrained S-peptide in complex with RNAse S. The scope of the acetone-linked peptides was further explored through the generation of N-terminus to side chain macrocycles and a new approach for generating fused macrocycles (bicycles). Together, these studies suggest that acetone linking is generally applicable to peptide macrocycles with a specific utility in the synthesis of stabilized helices that incorporate functional tags.
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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.