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Amidación enantioselectiva catalizada por metalloenzimas por medio de la inserción de nitreno en enlaces C3H no

Kun Yu1, Zhi Zou1, Nico V Igareta1

  • 1Department of Chemistry, University of Basel, Mattenstrasse 24a, BPR 1096, Basel CH-4058, Switzerland.

Journal of the American Chemical Society
|July 20, 2023
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Resumen

Una metaloenzima artificial (ArM) permite la amidación C-H enantioselectiva de los enlaces C ((sp3) -H no activados. Este avance logró una alta actividad y selectividad, allanando el camino para la síntesis de moléculas nuevas que contienen nitrógeno.

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Área de la Ciencia:

  • Catálisis
  • La bioquímica
  • Química orgánica

Sus antecedentes:

  • La amidación C-H enantioselectiva es crucial para sintetizar compuestos valiosos que contienen nitrógeno.
  • Se han desarrollado métodos catalíticos tanto enzimáticos como homogéneos para la amidación C-H.

Objetivo del estudio:

  • Desarrollar una nueva metalloenzima artificial (ARM) para la amidación C-H enantioselectiva.
  • Optimizar el ARM para una mayor actividad y selectividad.

Principales métodos:

  • Se ancló un complejo de iridio dentro de la estreptavidina para crear el ARM.
  • Se realizó una optimización quimiogenética del cofactor de iridio y de la streptavidina.
  • Se emplearon cálculos de cristalografía de rayos X y mecánica cuántica-molecular (QM-MM).

Principales resultados:

  • El ARM catalizó con éxito la amidación enantioselectiva de enlaces C ((sp3) -H no activados.
  • A través de la optimización se lograron mejoras significativas en la actividad y en la enantioselectividad.
  • Se obtuvieron cifras de facturación (TON) superiores a 700 y un exceso enantiomérico (ee) del 92%.

Conclusiones:

  • El ARM desarrollado, una insertasa de nitreno artificial (ANIasa), es un catalizador altamente eficaz para la amidación de C-H.
  • Las interacciones de la segunda esfera de coordinación dentro del ARM son críticas para su mejor rendimiento catalítico.
  • Este trabajo proporciona información sobre el diseño de enzimas metálicas avanzadas para transformaciones químicas complejas.