ArticleJournal of the American Chemical Society2021
Photoenzymatic Synthesis of α-Tertiary Amines by Engineered Flavin-Dependent "Ene"-Reductases.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
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Who cites it
37 citing papers in PubMed, 88 citations in OpenAlex.
- Internally Directed Stereochemical Alteration of Alkene Dihalogenation.The Journal of organic chemistry · 2026Article
- Stereoselective cyano translocation reaction enabled by photoenzymatic catalysis.Nature communications · 2026Article
- The Cross-Species Implantable ATP Battery Inspired by Photosynthesis for Application in Diseases.International journal of nanomedicine · 2026Review
- Designing and Engineering Enzymes for New-to-Nature Photobiocatalysis.Methods in molecular biology (Clifton, N.J.) · 2026Review
- Photoenzymatic catalysis enables enantioselective radical dearomative spirocyclization.Nature communications · 2025Article
- Aromatic Coupling Reactions Catalyzed by "ene"-Reductase under Visible Light Irradiation.ACS omega · 2025Article
- Cofactor-independent photo-enzymatic reductions with water mediated by reductive graphene quantum dots.Nature communications · 2025Article
- Trifluoroethanol-assisted asymmetric propargylic hydrazination to α-tertiary ethynylhydrazines enabled by sterically confined pyridinebisoxazolines.Nature communications · 2025Article
- Transitioning enzyme catalysis towards photocatalysis.Philosophical transactions. Series A, Mathematical, physical, and engineering sciences · 2025Review
- A metalloenzyme platform for catalytic asymmetric radical dearomatization.Nature chemistry · 2024Article
- Threonine Aldolase-Catalyzed Enantioselective α-Alkylation of Amino Acids through Unconventional Photoinduced Radical Initiation.Journal of the American Chemical Society · 2024Article
- Stereodivergent photobiocatalytic radical cyclization through the repurposing and directed evolution of fatty acid photodecarboxylases.Nature chemistry · 2024Article
- Catalytic Asymmetric Access to Structurally DiverseJACS Au · 2024Article
- From Ground-State to Excited-State Activation Modes: Flavin-Dependent "Ene"-Reductases Catalyzed Non-natural Radical Reactions.Accounts of chemical research · 2024Review
- Biocatalytic, Enantioenriched Primary Amination of Tertiary C-H Bonds.Nature catalysis · 2024Article
- Asymmetric Synthesis of α-Chloroamides via Photoenzymatic Hydroalkylation of Olefins.Journal of the American Chemical Society · 2024Article
- Evidence of a Distinctive Enantioselective Binding Mode for the Photoinduced Radical Cyclization of α-Chloroamides in Ene-Reductases.ACS catalysis · 2023Article
- Scope and Mechanistic Probe into Asymmetric Synthesis of α-Trisubstituted-α-Tertiary Amines by Rhodium Catalysis.Journal of the American Chemical Society · 2023Article
- Tailored photoenzymatic systems for selective reduction of aliphatic and aromatic nitro compounds fueled by light.Nature communications · 2023Article
- Recent Advances in the Enantioselective Radical Reactions.Molecules (Basel, Switzerland) · 2023Review
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Authors and funding
5 authors at 2 institutions in 1 country.
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Abstract
α-Tertiary amines are a common motif in pharmaceutically important molecules but are challenging to prepare using asymmetric catalysis. Here, we demonstrate engineered flavin-dependent 'ene'-reductases (EREDs) can catalyze radical additions into oximes to prepare this motif. Two different EREDs were evolved into competent catalysts for this transformation with high levels of stereoselectivity. Mechanistic studies indicate that the oxime contributes to the enzyme templated charge-transfer complex formed between the substrate and cofactor. These products can be further derivatized to prepare a variety of motifs, highlighting the versatility of ERED photoenzymatic catalysis for organic synthesis.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.