ArticleNature chemistry2021
Dual-function enzyme catalysis for enantioselective carbon-nitrogen bond formation.
Article in Nature chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 32 papers.
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Who cites it
32 citing papers in PubMed, 91 citations in OpenAlex.
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- Biocatalytic Synthesis of N-Protected α-Amino Acids through 1,3-Nitrogen Migration by Nonheme Iron Enzymes.Journal of the American Chemical Society · 2025Article
- Cu-Catalyzed Asymmetric Carbene Insertion into N-H, O-H, and S-H Bonds: Challenging the Existing Mechanistic Dogma.JACS Au · 2025Article
- Multifunctional chiral silanol ligands for enantioselective catalysis.Chemical science · 2025Article
- Iron-Catalyzed Intermolecular N-H Insertion Using Acceptor-Acceptor Carbenes Derived from Iodonium Ylides.Organic letters · 2025Article
- Experimental and Computational Evaluation of Nicotinamide Cofactor Biomimetics.ACS chemical biology · 2025Article
- Designing Enzymatic Reactivity with an Expanded Palette.Chembiochem : a European journal of chemical biology · 2025Review
- Exploiting Archaeal/Thermostable Enzymes in Synthetic Chemistry: Back to the Future?ChemCatChem · 2024Article
- Stereodivergent Synthesis of Pyridyl Cyclopropanes via Enzymatic Activation of Pyridotriazoles.Journal of the American Chemical Society · 2024Article
- Unlocking the function promiscuity of old yellow enzyme to catalyze asymmetric Morita-Baylis-Hillman reaction.Nature communications · 2024Article
- CYP3A Mediates an Unusual C(spAngewandte Chemie (International ed. in English) · 2024Article
- Choose Your Own Adventure: A Comprehensive Database of Reactions Catalyzed by Cytochrome P450 BM3 Variants.ACS catalysis · 2024Review
- Heterogeneous Rhodium Single-Atom-Site Catalyst Enables Chemoselective Carbene N-H Bond Insertion.Journal of the American Chemical Society · 2024Article
- Multifunctional Biocatalysts for Organic Synthesis.Journal of the American Chemical Society · 2024Review
- Biocatalytic Construction of Chiral Pyrrolidines and Indolines via Intramolecular C(spACS central science · 2023Article
- Role of mutations in a chemoenzymatic enantiodivergent C(spChemical science · 2023Article
- Carbene Radicals in Transition-Metal-Catalyzed Reactions.ACS catalysis · 2023Review
- First and second sphere interactions accelerate non-nativeChemical communications (Cambridge, England) · 2023Article
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Chiral amines can be made by insertion of a carbene into an N-H bond using two-catalyst systems that combine a transition metal-based carbene-transfer catalyst and a chiral proton-transfer catalyst to enforce stereocontrol. Haem proteins can effect carbene N-H insertion, but asymmetric protonation in an active site replete with proton sources is challenging. Here we describe engineered cytochrome P450 enzymes that catalyse carbene N-H insertion to prepare biologically relevant α-amino lactones with high activity and enantioselectivity (up to 32,100 total turnovers, >99% yield and 98% e.e.). These enzymes serve as dual-function catalysts, inducing carbene transfer and promoting the subsequent proton transfer with excellent stereoselectivity in a single active site. Computational studies uncover the detailed mechanism of this new-to-nature enzymatic reaction and explain how active-site residues accelerate this transformation and provide stereocontrol.
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Registered trials
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.