Reaction Discovery Using Spectroscopic Insights from an Enzymatic C–H Amination Intermediate

Das, Anuvab; Gao, Shilong; Lal, Ravi G.; Hicks, Madeline H.; Oyala, Paul H.; Arnold, Frances H.

doi:10.1021/jacs.4c05761

Title: Reaction Discovery Using Spectroscopic Insights from an Enzymatic C–H Amination Intermediate

Journal Article · Mon Jul 22 00:00:00 UTC 2024 · Journal of the American Chemical Society

DOI: https://doi.org/10.1021/jacs.4c05761 · OSTI ID:2406462

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^[2]; Lal, Ravi G. ^[3]; Hicks, Madeline H. ^[3];

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California Institute of Technology (CalTech), Pasadena, CA (United States); California Institute of Technology
California Institute of Technology (CalTech), Pasadena, CA (United States); Moderna, Boston, MA (United States)
California Institute of Technology (CalTech), Pasadena, CA (United States)

Engineered hemoproteins can selectively incorporate nitrogen from nitrene precursors like hydroxylamine, O-substituted hydroxylamines, and organic azides into organic molecules. Although iron-nitrenoids are often invoked as the reactive intermediates in these reactions, their innate reactivity and transient nature have made their characterization challenging. Here we characterize an iron-nitrosyl intermediate generated from NH₂OH within a protoglobin active site that can undergo nitrogen-group transfer catalysis, using UV–vis, electron paramagnetic resonance (EPR) spectroscopy, and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) techniques. The mechanistic insights gained led to the discovery of aminating reagents—nitrite (NO₂^–), nitric oxide (NO), and nitroxyl (HNO)—that are new to both nature and synthetic chemistry. Based on the findings, we propose a catalytic cycle for C–H amination inspired by the nitrite reductase pathway. Furthermore, this study highlights the potential of engineered hemoproteins to access natural nitrogen sources for sustainable chemical synthesis and offers a new perspective on the use of biological nitrogen cycle intermediates in biocatalysis.

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Research Organization:: California Institute of Technology (CalTech), Pasadena, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0021141

OSTI ID:: 2406462

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 30 Vol. 146; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
biocatalysis
directed evolution
electron paramagnetic resonance
nitrene transfer
nitrite reductase
nitrogen
organic reactions
peptides and proteins
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Title: Reaction Discovery Using Spectroscopic Insights from an Enzymatic C–H Amination Intermediate

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