ArticleAngewandte Chemie (International ed. in English)2019
Diketopiperazine Formation in Fungi Requires Dedicated Cyclization and Thiolation Domains.
Article in Angewandte Chemie (International ed. in English), 2019. 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, 38 citations in OpenAlex.
- Natural products shape microbial ecology and disease in the cystic fibrosis airway.Natural product reports · 2026Review
- Biosynthesis of a Novel Diketopiperazine Aspkyncin Incorporating a Kynurenine Unit fromJournal of fungi (Basel, Switzerland) · 2025Article
- Functional diversification of epidithiodiketopiperazine methylation and oxidation towards pathogenic fungi.Mycology · 2025Article
- Neochetracin: An Unusual Chetracin-Type Epithiodiketopiperazine Derivative Produced by the FungusACS omega · 2024Article
- Enzymatic Benzofuranoindoline Formation in the Biosynthesis of the Strained Bridgehead Bicyclic Dipeptide (+)-Azonazine A.Angewandte Chemie (International ed. in English) · 2023Article
- Natural and engineered cyclodipeptides: Biosynthesis, chemical diversity, and engineering strategies for diversification and high-yield bioproduction.Engineering microbiology · 2023Review
- Epipolythiodioxopiperazine-Based Natural Products: Building Blocks, Biosynthesis and Biological Activities.Chembiochem : a European journal of chemical biology · 2022Review
- Unexpected assembly machinery for 4(3H)-quinazolinone scaffold synthesis.Nature communications · 2022Article
- Genetic Survey of Psilocybe Natural Products.Chembiochem : a European journal of chemical biology · 2022Article
- Sulfur-Containing Compounds from Endophytic Fungi: Sources, Structures and Bioactivities.Journal of fungi (Basel, Switzerland) · 2022Review
- Integration of In Silico and In Vitro Analysis of Gliotoxin Production Reveals a Narrow Range of Producing Fungal Species.Journal of fungi (Basel, Switzerland) · 2022Article
- An interpreted atlas of biosynthetic gene clusters from 1,000 fungal genomes.Proceedings of the National Academy of Sciences of the United States of America · 2021Article
- Biosynthetic Cyclization Catalysts for the Assembly of Peptide and Polyketide Natural Products.ChemCatChem · 2021Article
- Article
- Efficient nonenzymatic cyclization and domain shuffling drive pyrrolopyrazine diversity from truncated variants of a fungal NRPS.Proceedings of the National Academy of Sciences of the United States of America · 2019Article
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Authors and funding
9 authors at 4 institutions in 2 countries.
Funding
Abstract
Cyclization of linear dipeptidyl precursors derived from nonribosomal peptide synthetases (NRPSs) into 2,5-diketopiperazines (DKPs) is a crucial step in the biosynthesis of a large number of bioactive natural products. However, the mechanism of DKP formation in fungi has remained unclear, despite extensive studies of their biosyntheses. Here we show that DKP formation en route to the fungal virulence factor gliotoxin requires a seemingly extraneous couplet of condensation (C) and thiolation (T) domains in the NRPS GliP. In vivo truncation of GliP to remove the CT couplet or just the T domain abrogated production of gliotoxin and all other gli pathway metabolites. Point mutation of conserved active sites in the C and T domains diminished cyclization activity of GliP in vitro and abolished gliotoxin biosynthesis in vivo. Verified NRPSs of other fungal DKPs terminate with similar CT domain couplets, suggesting a conserved strategy for DKP biosynthesis by fungal NRPSs.
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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.