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Enzymatic Nitrogen Incorporation Using Hydroxylamine.

Shilong Gao1, Anuvab Das1, Edwin Alfonzo1

  • 1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

Journal of the American Chemical Society
|September 6, 2023
PubMed
Summary
This summary is machine-generated.

Researchers engineered a heme enzyme to activate hydroxylamine for sustainable nitrene transfer reactions, enabling efficient amine synthesis with water as the only byproduct.

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Area of Science:

  • Biocatalysis
  • Organic Chemistry
  • Enzyme Engineering

Background:

  • Hydroxylamine-derived reagents are used for nitrene transfer reactions but generate waste.
  • Activating hydroxylamine (NH2OH) offers a sustainable route to amine synthesis with water as the sole byproduct.
  • Enzymatic use of hydroxylamine for nitrogen incorporation in biosynthesis is currently unknown.

Purpose of the Study:

  • To engineer a heme enzyme capable of utilizing hydroxylamine for nitrene transfer.
  • To develop a sustainable method for amine synthesis using inexpensive commodity chemicals.
  • To explore the potential for discovering natural enzymes involved in hydroxylamine-based amination.

Main Methods:

  • Directed evolution of *Pyrobaculum arsenaticum* protoglobin.
  • Utilizing hydroxylammonium chloride as the hydroxylamine source.
  • Mechanistic studies to elucidate the reaction pathway.

Main Results:

  • An engineered heme enzyme efficiently performs nitrene transfer using hydroxylammonium chloride.
  • The enzyme catalyzes benzylic C-H primary amination and styrene aminohydroxylation.
  • Mechanistic studies revealed a stepwise radical pathway initiated by hydrogen atom transfer.

Conclusions:

  • Engineered heme enzymes can utilize hydroxylamine for nitrene transfer, offering a sustainable alternative to traditional reagents.
  • This work expands the repertoire of nitrene transferases and suggests potential for discovering novel natural enzymes.
  • The findings pave the way for greener synthesis of nitrogen-containing compounds.