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Reutilización de las hemoproteínas para la transferencia asimétrica de átomos de H catalizados por metales

Xiang Zhang^1,2, Dongping Chen^1,2, María Álvarez¹

¹Department of Chemistry, University of Basel, Basel, Switzerland.

|July 31, 2025

Resumen

Los científicos reutilizaron las enzimas del citocromo P450 para la catálisis asimétrica de transferencia de átomos de hidrógeno de metal (MHAT). La evolución dirigida creó nuevas enzimas para sintetizar compuestos cíclicos quirales a partir de alquenos y otros sustratos con alta enantioselectividad.

Área de la Ciencia:

Biocatálisis
Química orgánica
Ingeniería de enzimas

Sus antecedentes:

Los hidruros de metales de transición son vitales en las reacciones de hidrofuncionalización.
La transferencia de átomos de hidrógeno de metal-hidruro (MHAT) permite la hidrofuncionalización radical de los alquenos no activados.
La MHAT asimétrica es un desafío debido a las débiles interacciones catalizador-radical.

Objetivo del estudio:

Reutilizar las enzimas del citocromo P450 (CYP) para la catálisis asimétrica de MHAT.
Para desarrollar una nueva reacción asimétrica a la naturaleza.
Ampliar el ámbito de aplicación de la biocatálisis de radicales asimétricos.

Principales métodos:

Evolución dirigida de P450_BM3 para crear un catalizador mutante triple.
Utilizando condiciones aeróbicas de toda la célula para la catálisis.
Investigaciones mecanicistas para elucidar la vía de reacción.

Principales resultados:

El P450_BM3 diseñado catalizó la ciclización radical MHAT de alquenos no activados con una relación enantiomérica de hasta 98: 2.
Se sintetizaron diversos compuestos cíclicos, incluidas las pirrolidinas y las piperidinas.
El P450 _BM3 reutilizado convirtió con éxito hidrazonas, oximas y nitriles en productos enriquecidos con enantio.
La evolución dirigida de CYP119 produjo una MHATasa estereocomplementaria.

Conclusiones:

Las enzimas del citocromo P450 se pueden reutilizar con éxito para la MHAT asimétrica.
La evolución dirigida es una herramienta poderosa para crear nuevos biocatalizadores para reacciones radicales.
Este trabajo amplía el potencial de las metalenzimas en la biocatálisis de radicales asimétricos.

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