ArticleAngewandte Chemie (International ed. in English)2021
Enzyme-Primed Native Chemical Ligation Produces Autoinducing Cyclopeptides in Clostridia.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 22 citations in OpenAlex.
- Structural and Functional Siderophore Remodeling by Enzymatic Delipidation.Angewandte Chemie (International ed. in English) · 2026Article
- Autoinducing peptides regulate antibiotic production to potentially shape root microbiome.Science advances · 2025Article
- Large-scale biosynthetic analysis of human microbiomes reveals diverse protective ribosomal peptides.Nature communications · 2025Article
- A short-lived peptide signal regulates cell-to-cell communication in Listeria monocytogenes.Communications biology · 2024Article
- Characterization of an Autoinducing Peptide Signal Reveals Highly Efficacious Synthetic Inhibitors and Activators of Quorum Sensing and Biofilm Formation inBiochemistry · 2023Article
- Chemical and biomolecular insights into theIsrael journal of chemistry · 2023Article
- Enhancing Auxiliary-Mediated Native Chemical Ligation at Challenging Junctions with Pyridine Scaffolds.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Cleavage Off-Loading and Post-assembly-Line Conversions Yield Products with Unusual Termini during Biosynthesis.ACS chemical biology · 2022Article
- Alternative Benzoxazole Assembly Discovered in Anaerobic Bacteria Provides Access to Privileged Heterocyclic Scaffold.Angewandte Chemie (International ed. in English) · 2022Article
- Inner residues of macrothiolactone in autoinducer peptides I/IV circumvent spontaneousRSC chemical biology · 2022Article
- Enzyme-Primed Native Chemical Ligation Produces Autoinducing Cyclopeptides in Clostridia.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
11 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Clostridia coordinate many important processes such as toxin production, infection, and survival by density-dependent communication (quorum sensing) using autoinducing peptides (AIPs). Although clostridial AIPs have been proposed to be (thio)lactone-containing peptides, their true structures remain elusive. Here, we report the genome-guided discovery of an AIP that controls endospore formation in Ruminiclostridium cellulolyticum. Through a combination of chemical synthesis and chemical complementation assays with a mutant strain, we reveal that the genuine chemical mediator is a homodetic cyclopeptide (cAIP). Kinetic analyses indicate that the mature cAIP is produced via a cryptic thiolactone intermediate that undergoes a rapid S→N acyl shift, in a manner similar to intramolecular native chemical ligation (NCL). Finally, by implementing a chemical probe in a targeted screen, we show that this novel enzyme-primed, intramolecular NCL is a widespread feature of clostridial AIP biosynthesis.
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