ArticleThe Journal of organic chemistry2018
Chemoselective Cyclopropanation over Carbene Y-H Insertion Catalyzed by an Engineered Carbene Transferase.
Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
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Who cites it
27 citing papers in PubMed, 82 citations in OpenAlex.
- Stabilized Carbon Radical-Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Mechanistic investigation of sustainable heme-inspired biocatalytic synthesis of cyclopropanes for challenging substrates.Communications chemistry · 2024Article
- Directed evolution ofChemical science · 2024Article
- Review
- Engineering an Oxygen-Binding Protein for Photocatalytic COAngewandte Chemie (International ed. in English) · 2023Article
- Intermolecular Organophotocatalytic Cyclopropanation of Unactivated Olefins.Journal of the American Chemical Society · 2023Article
- YfeX - A New Platform for Carbene Transferase Development with High Intrinsic Reactivity.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Exploring the enzyme-catalyzed synthesis of isotope labeled cyclopropanes.Journal of labelled compounds & radiopharmaceuticals · 2022Article
- Enantioselective Synthesis of α-Trifluoromethyl Amines via Biocatalytic N-H Bond Insertion with Acceptor-Acceptor Carbene Donors.Journal of the American Chemical Society · 2022Article
- Asymmetric Radical Process for General Synthesis of Chiral Heteroaryl Cyclopropanes.Journal of the American Chemical Society · 2021Article
- Origin and Control of Chemoselectivity in CytochromeJournal of the American Chemical Society · 2021Article
- Controllable stereoinversion in DNA-catalyzed olefin cyclopropanationChemical science · 2021Article
- De novo biosynthesis of a nonnatural cobalt porphyrin cofactor inProceedings of the National Academy of Sciences of the United States of America · 2021Article
- A Diverse Library of Chiral Cyclopropane Scaffolds via Chemoenzymatic Assembly and Diversification of Cyclopropyl Ketones.Journal of the American Chemical Society · 2021Article
- An Enzymatic Platform for the Highly Enantioselective and Stereodivergent Construction of Cyclopropyl-δ-lactones.Angewandte Chemie (International ed. in English) · 2020Article
- Enantioselective Synthesis of Chiral Amines via Biocatalytic Carbene N-H Insertion.ACS catalysis · 2020Article
- Organic solvent stability and long-term storage of myoglobin-based carbene transfer biocatalysts.Biotechnology and applied biochemistry · 2020Article
- Selective Functionalization of Aliphatic Amines via Myoglobin-catalyzed Carbene N-H Insertion.Synlett : accounts and rapid communications in synthetic organic chemistry · 2020Article
- Strategies for the expression and characterization of artificial myoglobin-based carbene transferases.Methods in enzymology · 2020Article
- A Continuing Career in Biocatalysis: Frances H. Arnold.ACS catalysis · 2019Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Hemoproteins have recently emerged as promising biocatalysts for promoting a variety of carbene transfer reactions including cyclopropanation and Y-H insertion (Y = N, S, Si, B). For these and synthetic carbene transfer catalysts alike, achieving high chemoselectivity toward cyclopropanation in olefin substrates bearing unprotected Y-H groups has proven remarkably challenging due to competition from the more facile carbene Y-H insertion reaction. In this report, we describe the development of a novel artificial metalloenzyme based on an engineered myoglobin incorporating a serine-ligated Co-porphyrin cofactor that is capable of offering high selectivity toward olefin cyclopropanation over N-H and Si-H insertion. Intramolecular competition experiments revealed a distinct and dramatically altered chemoselectivity of the Mb(H64V,V68A,H93S)[Co(ppIX)] variant in carbene transfer reactions compared to myoglobin-based variants containing the native histidine-ligated heme cofactor or other metal/proximal ligand substitutions. These studies highlight the functional plasticity of myoglobin as a "carbene transferase" and illustrate how modulation of the cofactor environment within this metalloprotein scaffold represents a valuable strategy for accessing carbene transfer reactivity not exhibited by naturally occurring hemoproteins or transition metal catalysts.
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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.