ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
Chemical and Genetic Studies on the Formation of Pyrrolones During the Biosynthesis of Cytochalasans.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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9 citing papers in PubMed.
- Investigating the versatility of cytochalasan cytochrome P450 monooxygenases using combinatorial biosynthesis reveals stereochemical restrictions.Fungal biology and biotechnology · 2026Article
- Article
- Synthesis of l-β-(6-azulenyl)alanine and the fluorescent actin disruptor (6-azuleno)chalasin H.RSC advances · 2025Article
- New Chaetoglobosins with Fungicidal Activity fromJournal of fungi (Basel, Switzerland) · 2025Article
- Structure and Biosynthesis of Perochalasins A-C, Open-Chain Merocytochalasans Produced by the Marine-Derived FungusJournal of natural products · 2024Article
- Berberine bridge enzyme-like oxidase-catalysed double bond isomerization acts as the pathway switch in cytochalasin synthesis.Nature communications · 2022Article
- Bioactive PKS-NRPS Alkaloids from the Plant-Derived Endophytic FungusMolecules (Basel, Switzerland) · 2021Article
- Secondary metabolite biosynthetic diversity in the fungal familyStudies in mycology · 2021Article
- Chemical and Genetic Studies on the Formation of Pyrrolones During the Biosynthesis of Cytochalasans.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
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5 authors.
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Abstract
A key step during the biosynthesis of cytochalasans is a proposed Knoevenagel condensation to form the pyrrolone core, enabling the subsequent 4+2 cycloaddition reaction that results in the characteristic octahydroisoindolone motif of all cytochalasans. In this work, we investigate the role of the highly conserved α,β-hydrolase enzymes PyiE and ORFZ during the biosynthesis of pyrichalasin H and the ACE1 metabolite, respectively, using gene knockout and complementation techniques. Using synthetic aldehyde models we demonstrate that the Knoevenagel condensation proceeds spontaneously but results in the 1,3-dihydro-2H-pyrrol-2-one tautomer, rather than the required 1,5-dihydro-2H-pyrrol-2-one tautomer. Taken together our results suggest that the α,β-hydrolase enzymes are essential for first ring cyclisation, but the precise nature of the intermediates remains to be determined.
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