ArticleNature communications2023
Enzyme-like polyene cyclizations catalyzed by dynamic, self-assembled, supramolecular fluoro alcohol-amine clusters.
Article in Nature communications, 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.
- Catalytic Asymmetric Cationic Geranyl Cyclizations.Journal of the American Chemical Society · 2026Article
- Atomically Precise Clusterzymes: A Programmable Optoelectronic Platform for Neuroscience.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Review
- Chemoenzymatic C,C-Bond Forming Cascades by Cryptic Vanadium Haloperoxidase Catalyzed Bromination.Organic letters · 2025Article
- Article
- Biocatalytic stereocontrolled head-to-tail cyclizations of unbiased terpenes as a tool in chemoenzymatic synthesis.Nature communications · 2024Article
- Controlling the regioselectivity of the bromolactonization reaction in HFIP.Chemical science · 2024Article
- Biomimetic and bioorthogonal nanozymes for biomedical applications.Nano convergence · 2023Review
- A biomimetic approach for the concise total synthesis of greenwaylactams A-C.Organic & biomolecular chemistry · 2023Article
- Biomimetic chlorine-induced polyene cyclizations harnessing hypervalent chloroiodane-HFIP assemblies.Chemical science · 2023Article
- Review
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
Terpene cyclases catalyze one of the most powerful transformations with respect to efficiency and selectivity in natural product (bio)synthesis. In such polyene cyclizations, structurally highly complex carbon scaffolds are built by the controlled ring closure of linear polyenes. Thereby, multiple C,C bonds and stereocenters are simultaneously created with high precision. Structural pre-organization of the substrate carbon chain inside the active center of the enzyme is responsible for the product- and stereoselectivity of this cyclization. Here, we show that in-situ formed fluorinated-alcohol-amine supramolecular clusters serve as artificial cyclases by triggering enzyme-like reactivity and selectivity by controlling substrate conformation in solution. Because of the dynamic nature of these supramolecular assemblies, a broad range of terpenes can be produced diastereoselectively. Mechanistic studies reveal a finely balanced interplay of fluorinated solvent, catalyst, and substrate as key to establishing nature's concept of a shape-selective polyene cyclization in organic synthesis.
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Registered trials
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