ArticleNature chemistry2023
An NmrA-like enzyme-catalysed redox-mediated Diels-Alder cycloaddition with anti-selectivity.
Article in Nature chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Covalent "Locking" of Prodrug Nanoassemblies via Thiol-Ene Click Crosslinking for Potent Antitumor Therapy.Advanced healthcare materials · 2026Article
- A programmable bifunctional flavoenzyme for direct amine-to-ester conversion.Science advances · 2026Article
- An enzymatic dual-oxa Diels-Alder reaction constructs the oxygen-bridged tricyclic acetal unit of (-)-anthrabenzoxocinone.Nature chemistry · 2025Article
- The Mutually Inspiring Biological and Chemical Synthesis of Fungal Bicyclo[2.2.2]diazaoctane Indole Alkaloids.Chemical reviews · 2025Review
- Enzymatic Ring Contraction for the Biosynthesis of Sulfur-Containing Cyclopentachromone.Journal of the American Chemical Society · 2025Article
- Review
- Discovery of a Potent Antiosteoporotic Drug Molecular Scaffold Derived fromACS central science · 2024Article
- Article
- Fungal P450 Deconstructs the 2,5-Diazabicyclo[2.2.2]octane RingJournal of the American Chemical Society · 2023Article
- Peroxidase-induced C-N bond formationGreen chemistry : an international journal and green chemistry resource : GC · 2023Article
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Authors and funding
16 authors.
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Abstract
The Diels-Alder cycloaddition is one of the most powerful approaches in organic synthesis and is often used in the synthesis of important pharmaceuticals. Yet, strictly controlling the stereoselectivity of the Diels-Alder reactions is challenging, and great efforts are needed to construct complex molecules with desired chirality via organocatalysis or transition-metal strategies. Nature has evolved different types of enzymes to exquisitely control cyclization stereochemistry; however, most of the reported Diels-Alderases have been shown to only facilitate the energetically favourable diastereoselective cycloadditions. Here we report the discovery and characterization of CtdP, a member of a new class of bifunctional oxidoreductase/Diels-Alderase, which was previously annotated as an NmrA-like transcriptional regulator. We demonstrate that CtdP catalyses the inherently disfavoured cycloaddition to form the bicyclo[2.2.2]diazaoctane scaffold with a strict α-anti-selectivity. Guided by computational studies, we reveal a NADP
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