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Engineering Chemoselectivity in Hemoprotein-Catalyzed Indole Amidation.

Oliver F Brandenberg1,2, David C Miller1, Ulrich Markel1,3

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

ACS Catalysis
|January 16, 2020
PubMed
Summary

Researchers engineered a cytochrome P450 enzyme for efficient C-H amidation of indoles using tosyl azide. Directed evolution enhanced selectivity and yield for nitrene transfer, overcoming side reactions in this novel biocatalytic approach.

Keywords:
BiocatalysisChemoselectivityCytochrome P450Indole AmidationNitrene Transfer

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Area of Science:

  • Biocatalysis
  • Enzyme Engineering
  • Organic Chemistry

Background:

  • Cytochrome P450 enzymes are versatile catalysts.
  • Nitrene transfer reactions are challenging in synthetic chemistry.
  • Developing selective biocatalysts for C-H functionalization is crucial.

Purpose of the Study:

  • To engineer a cytochrome P450 variant for selective C-H amidation of 1-methylindoles.
  • To overcome undesired side reactions like substrate reduction and triazole formation.
  • To expand the scope of hemoprotein nitrene transferases to heterocyclic compounds.

Main Methods:

  • Directed evolution was employed to optimize both heme and reductase domains of the P450 enzyme.
  • Mutagenesis strategies were used to improve catalytic efficiency and chemoselectivity.
  • Characterization of the engineered enzyme's activity, yield, and selectivity was performed.

Main Results:

  • An engineered P450 variant achieved high catalytic turnover (8400) and yield (90%) for indole amidation.
  • Chemoselectivity shifted significantly in favor of nitrene transfer over reduction or cycloaddition.
  • The enzyme successfully catalyzed C2-amidation of 1-methylindoles with tosyl azide via nitrene transfer.

Conclusions:

  • Directed evolution can overcome chemoselectivity challenges in non-natural enzymatic catalysis.
  • The engineered P450 scaffold is adaptable for challenging synthetic transformations.
  • This work expands hemoprotein nitrene transferase capabilities to heterocycles.