ArticleJournal of the American Chemical Society2021
A Diverse Library of Chiral Cyclopropane Scaffolds via Chemoenzymatic Assembly and Diversification of Cyclopropyl Ketones.
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 23 papers.
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Who cites it
23 citing papers in PubMed, 78 citations in OpenAlex.
- Biocatalytic Regioselective C-Formylation of Resorcinol Derivatives.Angewandte Chemie (International ed. in English) · 2026Article
- Electron donor-acceptor complex-driven photocatalyst-free synthesis of nitrocyclopropanes.RSC advances · 2025Article
- Automated Flow Synthesis of Artificial Heme Enzymes for Enantiodivergent Biocatalysis.Journal of the American Chemical Society · 2025Article
- Mechanistic investigation of sustainable heme-inspired biocatalytic synthesis of cyclopropanes for challenging substrates.Communications chemistry · 2024Article
- Biocatalytic Strategy for the Highly Stereoselective Synthesis of Fluorinated Cyclopropanes.Angewandte Chemie (International ed. in English) · 2024Article
- Stereodivergent Synthesis of Pyridyl Cyclopropanes via Enzymatic Activation of Pyridotriazoles.Journal of the American Chemical Society · 2024Article
- Biocatalytic strategy for the construction of spNature chemistry · 2024Article
- Chemoenzymatic synthesis of optically active α-cyclopropyl-pyruvates and cyclobutenoates via enzyme-catalyzed carbene transfer with diazopyruvate.Organic chemistry frontiers : an international journal of organic chemistry · 2024Article
- Mechanistic manifold in a hemoprotein-catalyzed cyclopropanation reaction with diazoketone.Nature communications · 2023Article
- Review
- Ligand-Metal Cooperation Enables Net Ring-Opening C-C Activation / Difunctionalization of Cyclopropyl Ketones.ACS catalysis · 2023Article
- Photosensitized OScience (New York, N.Y.) · 2023Article
- Dehaloperoxidase Catalyzed Stereoselective Synthesis of Cyclopropanol Esters.The Journal of organic chemistry · 2023Article
- Engineering an Oxygen-Binding Protein for Photocatalytic COAngewandte Chemie (International ed. in English) · 2023Article
- Enantioselective Single and Dual α-C-H Bond Functionalization of Cyclic Amines via Enzymatic Carbene Transfer.Journal of the American Chemical Society · 2023Article
- Preparation of Chiral Enantioenriched Densely Substituted Cyclopropyl Azoles, Amines, and Ethers via Formal SMolecules (Basel, Switzerland) · 2022Article
- Peroxidase Activity of Myoglobin Variants Reconstituted with Artificial Cofactors.Chembiochem : a European journal of chemical biology · 2022Article
- Highly stereoselective and enantiodivergent synthesis of cyclopropylphosphonates with engineered carbene transferases.Chemical science · 2022Article
- Designing Artificial Metalloenzymes by Tuning of the Environment beyond the Primary Coordination Sphere.Chemical reviews · 2022Review
- Organometallic catalysis in aqueous and biological environments: harnessing the power of metal carbenes.Chemical science · 2022Review
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4 authors at 1 institution in 1 country.
Funding
Abstract
Chiral cyclopropane rings are key pharmacophores in pharmaceuticals and bioactive natural products, making libraries of these building blocks a valuable resource for drug discovery and development campaigns. Here, we report the development of a chemoenzymatic strategy for the stereoselective assembly and structural diversification of cyclopropyl ketones, a highly versatile yet underexploited class of functionalized cyclopropanes. An engineered variant of sperm whale myoglobin is shown to enable the highly diastereo- and enantioselective construction of these molecules via olefin cyclopropanation in the presence of a diazoketone carbene donor reagent. This biocatalyst offers a remarkably broad substrate scope, catalyzing this reaction with high stereoselectivity across a variety of vinylarene substrates as well as a range of different α-aryl and α-alkyl diazoketone derivatives. Chemical transformation of these enzymatic products enables further diversification of these molecules to yield a collection of structurally diverse cyclopropane-containing scaffolds in enantiopure form, including core motifs found in drugs and natural products as well as novel structures. This work illustrates the power of combining abiological biocatalysis with chemoenzymatic synthesis for generating collections of optically active scaffolds of high value for medicinal chemistry and drug discovery.
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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.