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Inserción enzimática de nitrógeno en enlaces C-H no activados

Soumitra V Athavale1, Shilong Gao1, Anuvab Das1

  • 1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California91125, United States.

Journal of the American Chemical Society
|October 4, 2022
PubMed
Resumen

Los investigadores desarrollaron nuevas enzimas para la aminación y amidación selectiva de enlaces C-H, un nuevo enfoque bioquímico para la incorporación de nitrógeno a partir de precursores saturados.

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Área de la Ciencia:

  • Biocatálisis
  • Ingeniería de enzimas
  • Química orgánica

Sus antecedentes:

  • La funcionalización selectiva de los enlaces alifáticos C-H es crucial para la síntesis química, pero es un desafío.
  • La funcionalización enzimática del nitrógeno de los enlaces C-H es actualmente desconocida en la naturaleza.
  • Los métodos sintéticos para la aminación/amidación selectiva de C-H son limitados.

Objetivo del estudio:

  • Desarrollar nuevas enzimas para la aminación y amidación selectivas de enlaces C ((sp3) -H no activados.
  • Explorar la evolución dirigida para crear transferasas de nitreno nuevas en la naturaleza.
  • Establecer una nueva vía bioquímica para la incorporación de nitrógeno.

Principales métodos:

  • Evolución dirigida de las transferasas de nitreno que contienen hemo.
  • Ensayos enzimáticos con varios sustratos, incluidos el metil- y el etilciclohexano.
  • Efectos cinéticos de los isótopos (EIC) y estudios computacionales (simulaciones MD).

Principales resultados:

  • Las enzimas evolucionadas demuestran una aminación y una amidación selectivas de los sitios C ((sp3) -H no activados.
  • Se ha demostrado la desimetrización de metil- y etilciclohexano con una selectividad divergente.
  • Las enzimas evolucionadas exhiben una amplia promiscuidad de sustratos.

Conclusiones:

  • Se han desarrollado nuevas transferasas de nitreno capaces de la aminación/amidación selectiva de C-H.
  • El mecanismo implica una vía radical gradual con HAT y rebote radical.
  • Estas enzimas ofrecen una nueva estrategia bioquímica para sintetizar compuestos que contienen nitrógeno.