ArticleChembiochem : a European journal of chemical biology2020
Flavin-Dependent Monooxygenases NotI and NotI' Mediate Spiro-Oxindole Formation in Biosynthesis of the Notoamides.
Article in Chembiochem : a European journal of chemical biology, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 33 citations in OpenAlex.
- Flavin Hydroperoxide and Semiquinone: Structures and Biomimetic Activity.Journal of the American Chemical Society · 2026Article
- Investigating Opioid Receptor Activity through Biocatalytic Halogenation and Oxidation of Mitragynine.ACS chemical biology · 2026Article
- Flavin-dependent monooxygenases as versatile biocatalysts in biomanufacturing: mechanisms, engineering, and applications.Biotechnology for biofuels and bioproducts · 2026Review
- Engineered Flavin-Dependent Halogenases Catalyze C-C Bond Formation via Enantioselective Semipinacol Rearrangement.Journal of the American Chemical Society · 2026Article
- The Mutually Inspiring Biological and Chemical Synthesis of Fungal Bicyclo[2.2.2]diazaoctane Indole Alkaloids.Chemical reviews · 2025Review
- Biocatalytic Stereoselective Oxidation of 2-Arylindoles.Journal of the American Chemical Society · 2024Article
- An NmrA-like enzyme-catalysed redox-mediated Diels-Alder cycloaddition with anti-selectivity.Nature chemistry · 2023Article
- Data Science-Driven Analysis of Substrate-Permissive Diketopiperazine Reverse Prenyltransferase NotF: Applications in Protein Engineering and Cascade Biocatalytic Synthesis of (-)-Eurotiumin A.Journal of the American Chemical Society · 2022Article
- Enzymatic Late-Stage Modifications: Better Late Than Never.Angewandte Chemie (International ed. in English) · 2021Review
- Enzymkatalysierte späte Modifizierungen: Besser spät als nie.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2021Review
- Structural basis of the stereoselective formation of the spirooxindole ring in the biosynthesis of citrinadins.Nature communications · 2021Article
- Enzyme evolution in fungal indole alkaloid biosynthesis.The FEBS journal · 2020Review
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Authors and funding
11 authors at 4 institutions in 3 countries.
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Abstract
The fungal indole alkaloids are a unique class of complex molecules that have a characteristic bicyclo[2.2.2]diazaoctane ring and frequently contain a spiro-oxindole moiety. While various strains produce these compounds, an intriguing case involves the formation of individual antipodes by two unique species of fungi in the generation of the potent anticancer agents (+)- and (-)-notoamide A. NotI and NotI' have been characterized as flavin-dependent monooxygenases that catalyze epoxidation and semi-pinacol rearrangement to form the spiro-oxindole center within these molecules. This work elucidates a key step in the biosynthesis of the notoamides and provides an evolutionary hypothesis regarding a common ancestor for production of enantiopure notoamides.
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