ArticleChemistry (Weinheim an der Bergstrasse, Germany)2022
Carrier Protein-Free Enzymatic Biaryl Coupling in Arylomycin A2 Assembly and Structure of the Cytochrome P450 AryC.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 34 citations in OpenAlex.
- Biosynthesis of the Biphenomycin Family of Potent Antibiotics.Angewandte Chemie (International ed. in English) · 2025Article
- The Biarylitides: Understanding the Structure and Biosynthesis of a Fascinating Class of Cytochrome P450 Modified RiPP Natural Products.Chembiochem : a European journal of chemical biology · 2025Review
- Bacterial Cytochrome P450 Catalyzed Macrocyclization of Ribosomal Peptides.ACS bio & med chem Au · 2024Review
- Total Synthesis FacilitatesJournal of the American Chemical Society · 2024Article
- An Engineered Biarylitide Cross-Linking P450 from RiPP Biosynthesis Generates Alternative Cyclic Peptides.Organic letters · 2024Article
- Non-Native Site-Selective Enzyme Catalysis.Chemical reviews · 2023Review
- A Chemoenzymatic Approach to Investigate Cytochrome P450 Cross-Linking in Glycopeptide Antibiotic Biosynthesis.Methods in molecular biology (Clifton, N.J.) · 2023Article
- Development of a P450 Fusion Enzyme for Biaryl Coupling in Yeast.ACS chemical biology · 2022Article
- Cytochrome P450Angewandte Chemie (International ed. in English) · 2022Article
- Carrier Protein-Free Enzymatic Biaryl Coupling in Arylomycin A2 Assembly and Structure of the Cytochrome P450 AryC.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
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10 authors at 3 institutions in 1 country.
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Abstract
The arylomycin antibiotics are potent inhibitors of bacterial type I signal peptidase. These lipohexapeptides contain a biaryl structural motif reminiscent of glycopeptide antibiotics. We herein describe the functional and structural evaluation of AryC, the cytochrome P450 performing biaryl coupling in biosynthetic arylomycin assembly. Unlike its enzymatic counterparts in glycopeptide biosynthesis, AryC converts free substrates without the requirement of any protein interaction partner, likely enabled by a strongly hydrophobic cavity at the surface of AryC pointing to the substrate tunnel. This activity enables chemo-enzymatic assembly of arylomycin A2 that combines the advantages of liquid- and solid-phase peptide synthesis with late-stage enzymatic cross-coupling. The reactivity of AryC is unprecedented in cytochrome P450-mediated biaryl construction in non-ribosomal peptides, in which peptidyl carrier protein (PCP)-tethering so far was shown crucial both in vivo and in vitro.
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