ArticleChembiochem : a European journal of chemical biology2016
Mutating a Highly Conserved Residue in Diverse Cytochrome P450s Facilitates Diastereoselective Olefin Cyclopropanation.
Article in Chembiochem : a European journal of chemical biology, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 35 papers.
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Who cites it
35 citing papers in PubMed, 75 citations in OpenAlex.
- PCA-Based Database Mining Enables the Discovery of Bacterial Carbene Transferases for Stereodivergent Cyclopropanation.Angewandte Chemie (International ed. in English) · 2026Article
- Computational design of generalist cyclopropanases with stereodivergent selectivity.Nature communications · 2026Article
- Mechanistic investigation of sustainable heme-inspired biocatalytic synthesis of cyclopropanes for challenging substrates.Communications chemistry · 2024Article
- Choose Your Own Adventure: A Comprehensive Database of Reactions Catalyzed by Cytochrome P450 BM3 Variants.ACS catalysis · 2024Review
- Designing Artificial Metalloenzymes by Tuning of the Environment beyond the Primary Coordination Sphere.Chemical reviews · 2022Review
- Engineered Myoglobin Catalysts for Asymmetric Intermolecular Cyclopropanation Reactions.Bulletin of Japan Society of Coordination Chemistry · 2022Article
- Navigating the Unnatural Reaction Space: Directed Evolution of Heme Proteins for Selective Carbene and Nitrene Transfer.Accounts of chemical research · 2021Review
- Unlocking the therapeutic potential of artificial metalloenzymes.Proceedings of the Japan Academy. Series B, Physical and biological sciences · 2020Review
- A Continuing Career in Biocatalysis: Frances H. Arnold.ACS catalysis · 2019Article
- Stereoselective Cyclopropanation of Electron-Deficient Olefins with a Cofactor Redesigned Carbene Transferase Featuring Radical Reactivity.ACS catalysis · 2019Article
- Biocatalytic Strategy for Highly Diastereo- and Enantioselective Synthesis of 2,3-Dihydrobenzofuran-Based Tricyclic Scaffolds.Angewandte Chemie (International ed. in English) · 2019Article
- Article
- Stereodivergent Intramolecular Cyclopropanation Enabled by Engineered Carbene Transferases.Journal of the American Chemical Society · 2019Article
- Characterization and structure-guided engineering of the novel versatile terpene monooxygenase CYP109Q5 from Chondromyces apiculatus DSM436.Microbial biotechnology · 2019Article
- Origin of high stereocontrol in olefin cyclopropanation catalyzed by an engineered carbene transferase.ACS catalysis · 2019Article
- Highly Diastereo- and Enantioselective Synthesis of Nitrile-Substituted Cyclopropanes by Myoglobin-Mediated Carbene Transfer Catalysis.Angewandte Chemie (International ed. in English) · 2018Article
- Chemoselective Cyclopropanation over Carbene Y-H Insertion Catalyzed by an Engineered Carbene Transferase.The Journal of organic chemistry · 2018Article
- Catalytic iron-carbene intermediate revealed in a cytochromeProceedings of the National Academy of Sciences of the United States of America · 2018Article
- An Artificial Heme Enzyme for Cyclopropanation Reactions.Angewandte Chemie (International ed. in English) · 2018Article
- Asymmetric Reductive Carbocyclization Using Engineered Ene Reductases.Angewandte Chemie (International ed. in English) · 2018Article
Corrections and comments
- Erratum issued
Authors and funding
6 authors at 3 institutions in 1 country.
Funding
Abstract
Cytochrome P450s and other heme-containing proteins have recently been shown to have promiscuous activity for the cyclopropanation of olefins using diazoacetate reagents. Despite the progress made thus far, engineering selective catalysts for all possible stereoisomers for the cyclopropanation reaction remains a considerable challenge. Previous investigations of a model P450 (P450BM3 ) revealed that mutation of a conserved active site threonine (Thr268) to alanine transformed the enzyme into a highly active and selective cyclopropanation catalyst. By incorporating this mutation into a diverse panel of P450 scaffolds, we were able to quickly identify enantioselective catalysts for all possible diastereomers in the model reaction of styrene with ethyl diazoacetate. Some alanine variants exhibited selectivities that were markedly different from the wild-type enzyme, with a few possessing moderate to high diastereoselectivity and enantioselectivities up to 97 % for synthetically challenging cis-cyclopropane diastereomers.
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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.