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Researchers engineered Aeropyrum pernix protoglobin (ApePgb) variants for biocatalytic carbene transfer from stable diazirines. This breakthrough enables new synthetic routes using previously challenging carbene precursors at room temperature.

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Area of Science:

  • Biocatalysis
  • Organic Synthesis
  • Protein Engineering

Background:

  • Biocatalytic carbene transfer is vital for asymmetric synthesis.
  • Limited stability of diazo compounds restricts product diversity.
  • Diazirines offer enhanced stability but resist catalytic activation.

Purpose of the Study:

  • To engineer Aeropyrum pernix protoglobin (ApePgb) variants for carbene transfer from diazirines.
  • To overcome limitations of existing carbene transfer catalysts.
  • To enable new synthetic transformations using stable carbene precursors.

Main Methods:

  • Protein engineering of ApePgb variants.
  • Microcrystal electron diffraction (MicroED) for structural analysis.
  • Demonstration of catalytic activity with aryl diazirines.

Main Results:

  • Engineered ApePgb variants catalyze selective carbene transfer from diazirines at room temperature.
  • Structural analysis reveals enhanced heme active site access.
  • Successful application in cyclopropanation, N-H insertion, and Si-H insertion reactions.

Conclusions:

  • Engineered ApePgb variants are the first catalysts for selective carbene transfer from diazirines.
  • This work expands the scope of biocatalytic carbene transfer.
  • Provides a new platform for synthesizing diverse chemical products.