ArticleJournal of the American Chemical Society2014
Enzyme-controlled nitrogen-atom transfer enables regiodivergent C-H amination.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 58 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
58 citing papers in PubMed.
- Stereoselective Synthesis of Aminals Through Enzyme-Catalyzed Intermolecular C(spAngewandte Chemie (International ed. in English) · 2026Article
- Design-Evolution Synergy Enables New-to-Nature Enzyme Chemistry.bioRxiv : the preprint server for biology · 2026Article
- Highly Stable Mn(V)-Nitrido and Nitrogen-Atom Transfer Reactivity within aJournal of the American Chemical Society · 2026Article
- Silver-catalysed intermolecular benzylic-selective C-H amidationChemical science · 2026Article
- Biocatalytic Radical C(spResearch square · 2026Article
- PCA-Based Database Mining Enables the Discovery of Bacterial Carbene Transferases for Stereodivergent Cyclopropanation.Angewandte Chemie (International ed. in English) · 2026Article
- Metabolic Engineering of the 5-Aminolevulinate Biosynthetic Pathway in E. coli Improves Efficiency of Hemoprotein-Based Biocatalysis.Angewandte Chemie (International ed. in English) · 2025Article
- Enzyme-catalyzed C(spRSC advances · 2025Article
- Structure-Function Analysis of the Self-Sufficient CYP102 Family Provides New Insights into Their Biochemistry.International journal of molecular sciences · 2025Article
- Highly Enantioselective Construction of Oxazolidinone Rings via Enzymatic C(spACS catalysis · 2025Article
- Iron Corrole-Catalyzed Intramolecular Amination Reactions of Alkyl Azides. Spectroscopic Characterization and Reactivity of [FeAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Choose Your Own Adventure: A Comprehensive Database of Reactions Catalyzed by Cytochrome P450 BM3 Variants.ACS catalysis · 2024Review
- Myoglobin-Catalyzed Azide Reduction Proceeds via an Anionic Metal Amide Intermediate.Journal of the American Chemical Society · 2024Article
- Stereoselective Construction of β-, γ-, and δ-Lactam Rings via Enzymatic C-H Amidation.Nature catalysis · 2024Article
- HowJACS Au · 2023Article
- Catalytic, asymmetric carbon-nitrogen bond formation using metal nitrenoids: from metal-ligand complexesChemical science · 2023Review
- Non-Native Site-Selective Enzyme Catalysis.Chemical reviews · 2023Review
- Directed Evolution of an Iron(II)- and α-Ketoglutarate-Dependent Dioxygenase for Site-Selective Azidation of Unactivated Aliphatic C-H Bonds.Angewandte Chemie (International ed. in English) · 2023Article
- Chemodivergent C(spNature catalysis · 2023Article
- Stereoselective Construction of β-, γ-, and δ-Lactam Rings via Enzymatic C-H Amidation.Research square · 2023Article
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Authors and funding
5 authors.
Funding
Abstract
We recently demonstrated that variants of cytochrome P450BM3 (CYP102A1) catalyze the insertion of nitrogen species into benzylic C-H bonds to form new C-N bonds. An outstanding challenge in the field of C-H amination is catalyst-controlled regioselectivity. Here, we report two engineered variants of P450BM3 that provide divergent regioselectivity for C-H amination-one favoring amination of benzylic C-H bonds and the other favoring homo-benzylic C-H bonds. The two variants provide nearly identical kinetic isotope effect values (2.8-3.0), suggesting that C-H abstraction is rate-limiting. The 2.66-Å crystal structure of the most active enzyme suggests that the engineered active site can preorganize the substrate for reactivity. We hypothesize that the enzyme controls regioselectivity through localization of a single C-H bond close to the iron nitrenoid.
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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.