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Catálisis de la formación de macrociclos con plantilla de Foldamer

Zebediah C Girvin¹, Mary Katherine Andrews¹, Xinyu Liu¹

¹Department of Chemistry, University of Wisconsin-Madison, Madison, WI, USA.

Science (New York, N.Y.)

|December 21, 2019

Resumen

Los investigadores desarrollaron un nuevo método bioinspirado para sintetizar macrociclos utilizando un plegador catalítico de péptidos. Este enfoque facilita el cierre del anillo a través de la formación de enlaces carbono-carbono, superando un desafío clave en la química orgánica.

Área de la Ciencia:

Química orgánica sintética
Catálisis
Química supramolecular

Sus antecedentes:

Los macrociclos (≥12 átomos) son vitales en medicina, fragancias y detección.
La síntesis eficiente del macrociclo es un desafío debido a los costos entrópicos y las reacciones intermoleculares competidoras.

Objetivo del estudio:

Presentar una nueva estrategia bioinspirada para la formación del macrociclo a través de la formación de enlaces carbono-carbono.
Para utilizar un pliegador catalítico de péptidos α/β para el diseño de reacciones de cierre de anillo.

Principales métodos:

Utilizando un catalizador de plegado de péptido α/β con una conformación helicoidal específica.
El foldamer cuenta con una diadamina catalizadora primaria-secundaria para promover las reacciones.
Utilizando las reacciones de aldol para la formación de macrociclos.

Principales resultados:

Con éxito sintetizó macrociclos con tamaños de anillo que van desde 14 a 22 átomos.
Demostró la utilidad del método en la síntesis del producto natural robustol.
El pliegador catalítico modela efectivamente el proceso de cierre del anillo.

Conclusiones:

La estrategia bioinspirada presentada ofrece una ruta eficiente hacia la síntesis de macrociclos.
Los foldamers catalíticos pueden superar los desafíos en la formación de anillos grandes.
Este método es prometedor para acceder a estructuras macrocíclicas complejas.

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