ArticleAdvanced synthesis & catalysis2017
Metal Substitution Modulates the Reactivity and Extends the Reaction Scope of Myoglobin Carbene Transfer Catalysts.
Article in Advanced synthesis & catalysis, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 58 papers.
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Who cites it
58 citing papers in PubMed, 162 citations in OpenAlex.
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- 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
- YfeX - A New Platform for Carbene Transferase Development with High Intrinsic Reactivity.Chemistry (Weinheim an der Bergstrasse, Germany) · 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
- An Artificial Metalloenzyme Based on a Copper Heteroscorpionate Enables spJournal of the American Chemical Society · 2022Article
- Review
- Biocatalytic One-Carbon Ring Expansion of Aziridines to Azetidines via a Highly Enantioselective [1,2]-Stevens Rearrangement.Journal of the American Chemical Society · 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
- Engineered and Artificial Metalloenzymes for Selective C-H Functionalization.Current opinion in green and sustainable chemistry · 2021Article
- New-to-nature chemistry from old protein machinery: carbene and nitrene transferases.Current opinion in biotechnology · 2021Review
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Engineered myoglobins have recently emerged as promising scaffolds for catalyzing carbene-mediated transformations. In this work, we investigated the effect of altering the metal center and its first-sphere coordination environment on the carbene transfer reactivity of myoglobin. To this end, we first established an efficient protocol for the recombinant expression of myoglobin variants incorporating metalloporphyrins with non-native metals, including second- and third-row transition metals (ruthenium, rhodium, iridium). Characterization of the cofactor-substituted myoglobin variants across three different carbene transfer reactions (cyclopropanation, N-H insertion, S-H insertion) revealed a major influence of the nature of metal center, its oxidation state and first-sphere coordination environment on the catalytic activity, stereoselectivity, and/or oxygen tolerance of these artificial metalloenzymes. In addition, myoglobin variants incorporating manganese- or cobalt-porphyrins were found capable of catalyzing an intermolecular carbene C-H insertion reaction involving phthalan and ethyl α-diazoacetate, a reaction not supported by iron-based myoglobins and previously accessed only using iridium-based (bio)catalysts. These studies demonstrate how modification of the metalloporphyrin cofactor environment provides a viable and promising strategy to enhance the catalytic properties and extend the reaction scope of myoglobin-based carbene transfer catalysts.
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