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La hidroxilación remota de C-H por una dioxigenasa dependiente del α-cetoglutarato permite una síntesis

Christian R Zwick¹, Hans Renata¹

¹Department of Chemistry, The Scripps Research Institute , 130 Scripps Way, Jupiter, Florida 33458, United States.

Journal of the American Chemical Society

|December 29, 2017

Resumen

Los investigadores caracterizaron una enzima dioxigenasa dependiente del alfa-cetoglutarato (Fe/αKG) que selectivamente hidroxila los aminoácidos alifáticos. Esta funcionalización enzimática C-H ofrece una nueva y poderosa herramienta para la síntesis de moléculas complejas.

Área de la Ciencia:

Química orgánica
Biocatálisis
Enzimología

Sus antecedentes:

La funcionalización selectiva de C-H en posiciones distales es un desafío significativo en la química orgánica sintética.
La naturaleza emplea enzimas para tales transformaciones, pero sus aplicaciones sintéticas están poco exploradas.

Objetivo del estudio:

Caracterizar funcionalmente una nueva dioxigenasa dependiente del alfa-cetoglutarato (Fe/αKG) para la hidroxilación selectiva de C-H.
Explorar la utilidad de la enzima en la síntesis de moléculas complejas y el desarrollo de nuevas estrategias sintéticas.

Principales métodos:

Caracterización funcional de la enzima, incluido el análisis cinético y el perfil del sustrato.
Aplicación de la enzima en la síntesis total de la manzacidina C y otros derivados de aminoácidos.

Principales resultados:

La enzima Fe/αKG caracterizada hidroxila selectivamente la posición δ de varios aminoácidos alifáticos.
La enzima exhibe una eficiencia catalítica superior y una promiscuidad de sustrato en comparación con las enzimas relacionadas.
Se logró una síntesis eficiente de manzacidina C y derivados complejos de aminoácidos.

Conclusiones:

Este estudio presenta una nueva enzima Fe/αKG con un potencial significativo para la funcionalización enzimática de C-H.
Los hallazgos proporcionan un plan para el uso de la hidroxilación Fe/αKG en la síntesis de moléculas complejas y el desarrollo de nuevos paradigmas sintéticos.

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