ArticleJournal of the American Chemical Society2017
Function and Structure of MalA/MalA', Iterative Halogenases for Late-Stage C-H Functionalization of Indole Alkaloids.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 44 papers.
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44 citing papers in PubMed, 79 citations in OpenAlex.
- Structural basis of regioselective double halogenation of the β-carboline tryptoline by the single-component halogenase AetF.Acta crystallographica. Section D, Structural biology · 2026Article
- Investigating Opioid Receptor Activity through Biocatalytic Halogenation and Oxidation of Mitragynine.ACS chemical biology · 2026Article
- On the Origin of Substrate Specificity of Enzymes from the Amidohydrolase Superfamily.Angewandte Chemie (International ed. in English) · 2026Article
- Precision Molecular Editing: Predicting Substrate Scope and Regiochemistry for CHEESY1, a Flavin Dependent Halogenase.ACS catalysis · 2025Article
- Structural Basis of Regioselective Bromination of Tricyclic Tryptoline by the Tryptophan Halogenase Thal.Chembiochem : a European journal of chemical biology · 2025Article
- Crystal structures and low-affinity complex formation of halogenase CtcP and FAD reductase CtcQ from the chlortetracycline biosynthetic pathway.Bioscience reports · 2025Article
- SsDiHal: discovery and engineering of a novel tryptophan dihalogenase.Journal of biological engineering · 2025Article
- The Mutually Inspiring Biological and Chemical Synthesis of Fungal Bicyclo[2.2.2]diazaoctane Indole Alkaloids.Chemical reviews · 2025Review
- Crystallographic and Thermodynamic Evidence of Negative Coupling in the Flavin-Dependent Tryptophan Halogenases AbeH and BorH.ACS omega · 2025Article
- Balance between photoreduction efficiency, cofactor affinity, and allosteric coupling of halogenase flavoenzymes.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2025Article
- Genomic Sequencing and Functional Analysis of the Ex-Type Strain ofJournal of fungi (Basel, Switzerland) · 2024Article
- Identifying and Engineering Flavin Dependent Halogenases for Selective Biocatalysis.Accounts of chemical research · 2024Article
- A modular and synthetic biosynthesis platform for de novo production of diverse halogenated tryptophan-derived molecules.Nature communications · 2024Article
- Non-Native Site-Selective Enzyme Catalysis.Chemical reviews · 2023Review
- Fungal P450 Deconstructs the 2,5-Diazabicyclo[2.2.2]octane RingJournal of the American Chemical Society · 2023Article
- Structural basis of regioselective tryptophan dibromination by the single-component flavin-dependent halogenase AetF.Acta crystallographica. Section D, Structural biology · 2023Article
- Enzymatic Late-Stage Halogenation of Peptides.Chembiochem : a European journal of chemical biology · 2023Article
- Naturally Occurring Organohalogen Compounds-A Comprehensive Review.Progress in the chemistry of organic natural products · 2023Review
- Mechanism of Action of Flavin-Dependent Halogenases.ACS catalysis · 2022Article
- Biosynthesis of rumbrins and inspiration for discovery of HIV inhibitors.Acta pharmaceutica Sinica. B · 2022Article
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15 authors at 6 institutions in 2 countries.
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Abstract
Malbrancheamide is a dichlorinated fungal indole alkaloid isolated from both Malbranchea aurantiaca and Malbranchea graminicola that belongs to a family of natural products containing a characteristic bicyclo[2.2.2]diazaoctane core. The introduction of chlorine atoms on the indole ring of malbrancheamide differentiates it from other members of this family and contributes significantly to its biological activity. In this study, we characterized the two flavin-dependent halogenases involved in the late-stage halogenation of malbrancheamide in two different fungal strains. MalA and MalA' catalyze the iterative dichlorination and monobromination of the free substrate premalbrancheamide as the final steps in the malbrancheamide biosynthetic pathway. Two unnatural bromo-chloro-malbrancheamide analogues were generated through MalA-mediated chemoenzymatic synthesis. Structural analysis and computational studies of MalA' in complex with three substrates revealed that the enzyme represents a new class of zinc-binding flavin-dependent halogenases and provides new insights into a potentially unique reaction mechanism.
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