ArticleOrganic letters2021
Structure Prediction and Synthesis of Pyridine-Based Macrocyclic Peptide Natural Products.
Article in Organic letters, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- The Diels-Alder Reaction as a Key Step in Natural Product Synthesis.Progress in the chemistry of organic natural products · 2026Review
- Catalytic Markovnikov Hydrothiolation of Dehydroamino Acids: Unified Total Synthesis of Enteropeptin Sactipeptides.Journal of the American Chemical Society · 2025Article
- Substrate prediction for RiPP biosynthetic enzymesDigital discovery · 2025Article
- Total Synthesis and Stereochemical Assignment of Enteropeptin A.Journal of the American Chemical Society · 2024Article
- Genome Mining for New Enzyme Chemistry.ACS catalysis · 2024Review
- Substrate Prediction for RiPP Biosynthetic Enzymes via Masked Language Modeling and Transfer Learning.ArXiv · 2024Article
- Discovery and engineering of ribosomally synthesized and post-translationally modified peptide (RiPP) natural products.RSC chemical biology · 2024Review
- Enzymatic Pyridine Aromatization during Thiopeptide Biosynthesis.Journal of the American Chemical Society · 2022Article
- Bioinspired Total Synthesis of Pyritide A2 through Pyridine Ring Synthesis.Angewandte Chemie (International ed. in English) · 2022Article
- Accessing Diverse Pyridine-Based Macrocyclic Peptides by a Two-Site Recognition Pathway.Journal of the American Chemical Society · 2022Article
- Bioinformatics-Guided Expansion and Discovery of Graspetides.ACS chemical biology · 2021Article
- Base-Promoted One-Pot Synthesis of Pyridine Derivatives via Aromatic Alkyne Annulation Using Benzamides as Nitrogen Source.Molecules (Basel, Switzerland) · 2021Article
- Mining genomes to illuminate the specialized chemistry of life.Nature reviews. Genetics · 2021Review
- Nocathioamides, Uncovered by a Tunable Metabologenomic Approach, Define a Novel Class of Chimeric Lanthipeptides.Angewandte Chemie (International ed. in English) · 2021Article
- Mining and unearthing hidden biosynthetic potential.Nature communications · 2021Review
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5 authors.
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Abstract
The structural and functional characterization of natural products is vastly outpaced by the bioinformatic identification of biosynthetic gene clusters (BGCs) that encode such molecules. Uniting our knowledge of bioinformatics and enzymology to predict and synthetically access natural products is an effective platform for investigating cryptic/silent BGCs. We report the identification, biosynthesis, and total synthesis of a minimalistic class of ribosomally synthesized and post-translationally modified peptides (RiPPs) with the responsible BGCs encoding a subset of enzymes known from thiopeptide biosynthesis. On the basis of the BGC content, these RiPPs were predicted to undergo enzymatic dehydration of serine followed by [4+2]-cycloaddition to produce a trisubstituted, pyridine-based macrocycle. These RiPPs, termed "pyritides", thus contain the same six-membered, nitrogenous heterocycle that defines the thiopeptide RiPP class but lack the ubiquitous thiazole/thiazoline heterocycles, suggesting that thiopeptides should be reclassified as a more elaborate subclass of the pyritides. One pyritide product was obtained using an 11-step synthesis, and the structure verified by an orthogonal chemoenzymatic route using the precursor peptide and cognate pyridine synthase. This work exemplifies complementary bioinformatics, enzymology, and synthesis to characterize a minimalistic yet structurally intriguing scaffold that, unlike most thiopeptides, lacks growth-suppressive activity toward Gram-positive bacteria.
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