ArticleProceedings of the National Academy of Sciences of the United States of America2017
Structural insights into enzymatic [4+2]
Article in Proceedings of the National Academy of Sciences of the United States of America, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.
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Who cites it
31 citing papers in PubMed.
- Systematic Categorization and Functional Diversity of Secondary Metabolites from Bacillus spp.: A Review.Probiotics and antimicrobial proteins · 2026Review
- Characterizing and engineering post-translational modifications with high-throughput cell-free expression.Nature communications · 2025Article
- An enzymatic dual-oxa Diels-Alder reaction constructs the oxygen-bridged tricyclic acetal unit of (-)-anthrabenzoxocinone.Nature chemistry · 2025Article
- Unexpected Transformations during Pyrroloiminoquinone Biosynthesis.Journal of the American Chemical Society · 2024Article
- A Compact Reprogrammed Genetic Code for De Novo Discovery of Proteolytically Stable Thiopeptides.Journal of the American Chemical Society · 2024Article
- Unexpected transformations during pyrroloiminoquinone biosynthesis.bioRxiv : the preprint server for biology · 2024Article
- Dehydroamino acid residues in bioactive natural products.Natural product reports · 2024Review
- AlphaFold Accurately Predicts the Structure of Ribosomally Synthesized and Post-Translationally Modified Peptide Biosynthetic Enzymes.Biomolecules · 2023Article
- Enzymatic Pyridine Aromatization during Thiopeptide Biosynthesis.Journal of the American Chemical Society · 2022Article
- Molecular mechanism underlying substrate recognition of the peptide macrocyclase PsnB.Nature chemical biology · 2021Article
- Molecular Basis for Two Stereoselective Diels-Alderases that Produce Decalin Skeletons*.Angewandte Chemie (International ed. in English) · 2021Article
- Conformational rearrangements enable iterative backbone N-methylation in RiPP biosynthesis.Nature communications · 2021Article
- Article
- Thiopeptides: antibiotics with unique chemical structures and diverse biological activities.The Journal of antibiotics · 2021Review
- Structure Prediction and Synthesis of Pyridine-Based Macrocyclic Peptide Natural Products.Organic letters · 2021Article
- New developments in RiPP discovery, enzymology and engineering.Natural product reports · 2021Review
- Nonspecific Heme-Binding Cyclase, AbmU, Catalyzes [4 + 2] Cycloaddition during Neoabyssomicin Biosynthesis.ACS omega · 2020Article
- Interception of the Bycroft-Gowland Intermediate in the Enzymatic Macrocyclization of Thiopeptides.Journal of the American Chemical Society · 2020Article
- Precursor peptide-targeted mining of more than one hundred thousand genomes expands the lanthipeptide natural product family.BMC genomics · 2020Article
- Minimal lactazole scaffold for in vitro thiopeptide bioengineering.Nature communications · 2020Article
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7 authors.
Funding
Abstract
The [4+2] cycloaddition reaction is an enabling transformation in modern synthetic organic chemistry, but there are only limited examples of dedicated natural enzymes that can catalyze this transformation. Thiopeptides (or more formally thiazolyl peptides) are a class of thiazole-containing, highly modified, macrocyclic secondary metabolites made from ribosomally synthesized precursor peptides. The characteristic feature of these natural products is a six-membered nitrogenous heterocycle that is assembled via a formal [4+2] cycloaddition between two dehydroalanine (Dha) residues. This heteroannulation is entirely contingent on enzyme activity, although the mechanism of the requisite pyridine/dehydropiperidine synthase remains to be elucidated. The unusual
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