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Ciclización de un solo pote a grandes macrociclos peptidomiméticos por plegamiento forzado generado in situ

Fei Gou¹, Di Shi¹, Bohan Kou¹

¹Department of Chemistry, College of Chemistry and Chemical Engineering, The MOE Key Laboratory of Spectrochemical Analysis and Instrumentation, and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), Xiamen University, Xiamen 361005, China.

Journal of the American Chemical Society

|April 10, 2023

Resumen

Los investigadores desarrollaron una nueva síntesis de una sola olla para grandes macrociclos peptidomiméticos utilizando porciones de amidiourea. Estos macrociclos muestran cambios conformacionales al unirse a los aniones y pueden eliminar los aniones sulfatados del agua.

Área de la Ciencia:

Química supramolecular
Síntesis orgánica
Ciencias de los materiales

Sus antecedentes:

Los macrociclos son cruciales para el reconocimiento molecular y el autoensamblaje.
La síntesis eficiente de macrociclos a través de enlaces covalentes irreversibles sigue siendo un desafío importante en la química.

Objetivo del estudio:

Desarrollar una vía sintética eficiente para los grandes macrociclos peptidomiméticos.
Investigar las propiedades de unión aniónica y la dinámica estructural de estos macrociclos.
Explorar la aplicación de estos macrociclos en la eliminación de aniones de las soluciones acuosas.

Principales métodos:

Síntesis de un solo recipiente que incluye acilhidrazina y diisotiocianato a base de aminoácidos bilaterales.
Generación in situ de motivos estructurales de giro β dentro de las fracciones de amidotiourea.
Purificación por filtración simple.
Cristalografía de rayos X para la caracterización estructural.
Espectroscopia de dicroísmo circular (CD) para el análisis conformacional.
Extracción líquido-líquido para la eliminación de aniones.

Principales resultados:

Se han sintetizado con éxito cuatro macrociclos peptidomiméticos quirales y aquirales en altos rendimientos (45-63%).
La cristalografía de rayos X reveló estructuras de giro β estabilizadas por enlaces de hidrógeno intramoleculares, lo que permite el cambio de conformación en la unión de aniones.
Se ha demostrado la unión selectiva de aniones sulfatados (SO4^2-) que conduce a cambios estructurales significativos y a la inversión de la señal CD.
Se ha conseguido una eliminación eficiente de los aniones sulfatados del agua mediante un método de extracción líquido-líquido mediado por macrociclos.

Conclusiones:

El protocolo sintético desarrollado proporciona un enfoque eficiente y factible para diversos macrociclos peptidomiméticos grandes.
Los macrociclos sintetizados exhiben una flexibilidad conformacional inducida por la unión de aniones única.
Estos macrociclos son prometedores para aplicaciones en la detección y eliminación de aniones, particularmente para los aniones sulfatados en el tratamiento del agua.

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