ArticleJournal of the American Chemical Society2014
Enantioselective imidation of sulfides via enzyme-catalyzed intermolecular nitrogen-atom transfer.
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 41 papers.
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Who cites it
41 citing papers in PubMed.
- Asymmetric synthesis of stereogenic-at-sulfur compounds via biocatalytic oxidation with Unspecific Peroxygenases.Nature communications · 2025Article
- Expanding the Terpene Universe: Synthetic Biology and Non-Natural Chemistry in Engineered Microorganisms.Molecules (Basel, Switzerland) · 2025Review
- Asymmetric catalytic reductive transformation of S(VI) to S(IV) for modular access to S(IV)-stereogenic sulfilimine derivatives.Science advances · 2025Article
- Creating novel metabolic pathways by protein engineering for bioproduction.Trends in biotechnology · 2025Review
- Highly Enantioselective Construction of Oxazolidinone Rings via Enzymatic C(spACS catalysis · 2025Article
- Review
- SelectiveACS catalysis · 2024Article
- Copper(I)-nitrene platform for chemoproteomic profiling of methionine.Nature communications · 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
- Heme Spin Distribution in the Substrate-Free and Inhibited Novel CYP116B5hd: A Multifrequency Hyperfine Sublevel Correlation (HYSCORE) Study.Molecules (Basel, Switzerland) · 2024Article
- Engineering C-C Bond Cleavage Activity into a P450 Monooxygenase Enzyme.Journal of the American Chemical Society · 2023Article
- Hijacking Chemical Reactions of P450 Enzymes for Altered Chemical Reactions and Asymmetric Synthesis.International journal of molecular sciences · 2022Review
- Designing Artificial Metalloenzymes by Tuning of the Environment beyond the Primary Coordination Sphere.Chemical reviews · 2022Review
- Engineered and Artificial Metalloenzymes for Selective C-H Functionalization.Current opinion in green and sustainable chemistry · 2021Article
- Enzymatic Late-Stage Modifications: Better Late Than Never.Angewandte Chemie (International ed. in English) · 2021Review
- Enzymkatalysierte späte Modifizierungen: Besser spät als nie.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2021Review
- Silver-Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions.Angewandte Chemie (International ed. in English) · 2021Article
- Navigating the Unnatural Reaction Space: Directed Evolution of Heme Proteins for Selective Carbene and Nitrene Transfer.Accounts of chemical research · 2021Review
- Catalytic Chemoselective Sulfimidation with an Electrophilic [CoChemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
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5 authors.
Funding
Abstract
Engineering enzymes with novel reaction modes promises to expand the applications of biocatalysis in chemical synthesis and will enhance our understanding of how enzymes acquire new functions. The insertion of nitrogen-containing functional groups into unactivated C-H bonds is not catalyzed by known enzymes but was recently demonstrated using engineered variants of cytochrome P450BM3 (CYP102A1) from Bacillus megaterium. Here, we extend this novel P450-catalyzed reaction to include intermolecular insertion of nitrogen into thioethers to form sulfimides. An examination of the reactivity of different P450BM3 variants toward a range of substrates demonstrates that electronic properties of the substrates are important in this novel enzyme-catalyzed reaction. Moreover, amino acid substitutions have a large effect on the rate and stereoselectivity of sulfimidation, demonstrating that the protein plays a key role in determining reactivity and selectivity. These results provide a stepping stone for engineering more complex nitrogen-atom-transfer reactions in P450 enzymes and developing a more comprehensive biocatalytic repertoire.
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