Nitrene transfers mediated by natural and artificial iron enzymes

Amines are ubiquitous in biology and pharmacy. As a consequence, introducing N functionalities in organic molecules is attracting strong continuous interest. The past decade has witnessed the emergence of very efficient and selective catalytic systems achieving this goal thanks to engineered hemopro...

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Bibliographic Details
Published in:Journal of inorganic biochemistry 2021-12, Vol.225, p.111613-111613, Article 111613
Main Authors: Coin, Guillaume, Latour, Jean-Marc
Format: Article
Language:English
Subjects:
Amination
Amines - chemical synthesis
Biocatalysis
Biochemistry, Molecular Biology
Catalysis
Chemical Sciences
Cyclization
Cytochrome P-450 Enzyme System - chemistry
Heme - chemistry
Hemeproteins - chemistry
Hemoprotein
Inorganic chemistry
Iron - chemistry
Iron enzyme
Life Sciences
Mechanism
Nitrene precursor
Nitrene transfer
Protein Engineering
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Summary:Amines are ubiquitous in biology and pharmacy. As a consequence, introducing N functionalities in organic molecules is attracting strong continuous interest. The past decade has witnessed the emergence of very efficient and selective catalytic systems achieving this goal thanks to engineered hemoproteins. In this review, we examine how these enzymes have been engineered focusing rather on the rationale behind it than the methodology employed. These studies are put in perspective with respect to in vitro and in vivo nitrene transfer processes performed by cytochromes P450. An emphasis is put on mechanistic aspects which are confronted to current molecular knowledge of these reactions. Forthcoming developments are delineated. Examples of nitrene transfer reactions catalyzed by natural and engineered hemoproteins. [Display omitted] •Historical coverage of biological nitrene transfer by hemoproteins.•Mechanistic understanding of generation of the nitrenoid species from nitrene precursors.•Comprehension of the electronic aspects of nitrene transfer reactions.
ISSN:0162-0134
1873-3344
DOI:10.1016/j.jinorgbio.2021.111613