ArticleAngewandte Chemie (International ed. in English)2018
Myoglobin-Catalyzed C-H Functionalization of Unprotected Indoles.
Article in Angewandte Chemie (International ed. in English), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
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Who cites it
37 citing papers in PubMed, 134 citations in OpenAlex.
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- 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
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- Engineered Myoglobin Catalysts for Asymmetric Intermolecular Cyclopropanation Reactions.Bulletin of Japan Society of Coordination Chemistry · 2022Article
- Engineered and Artificial Metalloenzymes for Selective C-H Functionalization.Current opinion in green and sustainable chemistry · 2021Article
- Crystal structure and Hirshfeld analysis of diethyl (2Acta crystallographica. Section E, Crystallographic communications · 2021Article
- Article
- Novel Arylindigoids by Late-Stage Derivatization of Biocatalytically Synthesized Dibromoindigo.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Navigating the Unnatural Reaction Space: Directed Evolution of Heme Proteins for Selective Carbene and Nitrene Transfer.Accounts of chemical research · 2021Review
- A Diverse Library of Chiral Cyclopropane Scaffolds via Chemoenzymatic Assembly and Diversification of Cyclopropyl Ketones.Journal of the American Chemical Society · 2021Article
- Multi C-H Functionalization Reactions of Carbazole Heterocycles via Gold-Catalyzed Carbene Transfer Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
Corrections and comments
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Authors and funding
4 authors at 2 institutions in 2 countries.
Funding
Abstract
Functionalized indoles are recurrent motifs in bioactive natural products and pharmaceuticals. While transition metal-catalyzed carbene transfer has provided an attractive route to afford C3-functionalized indoles, these protocols are viable only in the presence of N-protected indoles, owing to competition from the more facile N-H insertion reaction. Herein, a biocatalytic strategy for enabling the direct C-H functionalization of unprotected indoles is reported. Engineered variants of myoglobin provide efficient biocatalysts for this reaction, which has no precedents in the biological world, enabling the transformation of a broad range of indoles in the presence of ethyl α-diazoacetate to give the corresponding C3-functionalized derivatives in high conversion yields and excellent chemoselectivity. This strategy could be exploited to develop a concise chemoenzymatic route to afford the nonsteroidal anti-inflammatory drug indomethacin.
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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.