ArticleSynlett : accounts and rapid communications in synthetic organic chemistry2020
Selective Functionalization of Aliphatic Amines via Myoglobin-catalyzed Carbene N-H Insertion.
Article in Synlett : accounts and rapid communications in synthetic organic chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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11 citing papers in PubMed, 30 citations in OpenAlex.
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- YfeX - A New Platform for Carbene Transferase Development with High Intrinsic Reactivity.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Organometallic catalysis in aqueous and biological environments: harnessing the power of metal carbenes.Chemical science · 2022Review
- 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
- Dual-function enzyme catalysis for enantioselective carbon-nitrogen bond formation.Nature chemistry · 2021Article
- 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
- Strategies for the expression and characterization of artificial myoglobin-based carbene transferases.Methods in enzymology · 2020Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Engineered myoglobins have recently gained attention for their ability to catalyze a variety of abiological carbene transfer reactions including the functionalization of amines via carbene insertion into N-H bonds. However, the scope of myoglobin and other hemoprotein-based biocatalysts in the context of this transformation has been largely limited to aniline derivatives as the amine substrates and ethyl diazoacetate as the carbene donor reagent. In this report, we describe the development of an engineered myoglobin-based catalyst useful for promoting carbene N-H insertion reactions across a broad range of substituted benzylamines and α-diazo acetates with high efficiency (82-99% conversion), elevated catalytic turnovers (up to 7,000), and excellent chemoselectivity for the desired single insertion product (up to 99%). The scope of this transformation could be extended to cyclic aliphatic amines. These studies expand the biocatalytic toolbox available for the selective formation of C-N bonds, which are ubiquitous in many natural and synthetic bioactive compounds.
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