ArticleAngewandte Chemie (International ed. in English)2018
Asymmetric Reductive Carbocyclization Using Engineered Ene Reductases.
Article in Angewandte Chemie (International ed. in English), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- Interrupted Reactions in the Synthesis of Subrubine Alkaloids.ACS central science · 2026Article
- Propellane Alkaloid Biosynthesis and Total Synthesis via Interrupted Reaction Pathways.ACS central science · 2026Article
- Structure, Oligomerization, and Thermal Stability of a Recently Discovered Old Yellow Enzyme.Proteins · 2025Article
- Recent advances in enzymatic carbon-carbon bond formation.RSC advances · 2024Review
- Solvent concentration at 50% protein unfolding may reform enzyme stability ranking and process window identification.Nature communications · 2024Article
- Asymmetric Synthesis of Chiral 2-Cyclohexenones with Quaternary Stereocenters via Ene-Reductase Catalyzed Desymmetrization of 2,5-Cyclohexadienones.ACS catalysis · 2024Article
- Multifunctional Biocatalysts for Organic Synthesis.Journal of the American Chemical Society · 2024Review
- Asymmetric α-benzylation of cyclic ketones enabled by concurrent chemical aldol condensation and biocatalytic reduction.Nature communications · 2024Article
- Biocatalytic reduction of alkenes in micro-aqueous organic solvent catalysed by an immobilised ene reductase.Catalysis science & technology · 2023Article
- Mechanistic Insights into the Ene-Reductase-Catalyzed Promiscuous Reduction of Oximes to Amines.ACS catalysis · 2023Article
- Biocatalytic Asymmetric Cyclopropanations via Enzyme-Bound Iminium Ion Intermediates.Angewandte Chemie (International ed. in English) · 2021Article
- Enzymatic strategies for asymmetric synthesis.RSC chemical biology · 2021Review
- Lewis Base-Brønsted Acid-Enzyme Catalysis in Enantioselective Multistep One-Pot Syntheses.Angewandte Chemie (International ed. in English) · 2021Article
- Activation modes in biocatalytic radical cyclization reactions.Journal of industrial microbiology & biotechnology · 2021Review
- Biocatalytic Reduction Reactions from a Chemist's Perspective.Angewandte Chemie (International ed. in English) · 2021Review
- Broadening the scope of biocatalytic C-C bond formation.Nature reviews. Chemistry · 2020Article
- Emerging strategies for expanding the toolbox of enzymes in biocatalysis.Current opinion in chemical biology · 2020Review
- Some Biogenetic Considerations Regarding the Marine Natural Product (-)-Mucosin.Molecules (Basel, Switzerland) · 2019Article
- Photoexcitation of flavoenzymes enables a stereoselective radical cyclization.Science (New York, N.Y.) · 2019Article
- Asymmetric Reductive Carbocyclization Using Engineered Ene Reductases.Angewandte Chemie (International ed. in English) · 2018Article
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8 authors.
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Abstract
Ene reductases from the Old Yellow Enzyme (OYE) family reduce the C=C double bond in α,β-unsaturated compounds bearing an electron-withdrawing group, for example, a carbonyl group. This asymmetric reduction has been exploited for biocatalysis. Going beyond its canonical function, we show that members of this enzyme family can also catalyze the formation of C-C bonds. α,β-Unsaturated aldehydes and ketones containing an additional electrophilic group undergo reductive cyclization. Mechanistically, the two-electron-reduced enzyme cofactor FMN delivers a hydride to generate an enolate intermediate, which reacts with the internal electrophile. Single-site replacement of a crucial Tyr residue with a non-protic Phe or Trp favored the cyclization over the natural reduction reaction. The new transformation enabled the enantioselective synthesis of chiral cyclopropanes in up to >99 % ee.
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