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Alteración de los patrones de plegado de los trimadores de naftilo

Gregory J Gabriel¹, Steven Sorey, Brent L Iverson

¹Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA.

Journal of the American Chemical Society

|February 24, 2005

Resumen

Los investigadores diseñaron nuevos foldameres utilizando las interacciones aromáticas. Estos oligómeros sintéticos adoptan conformaciones distintas, como pliegues plisados o intercalativos, en el agua, lo que demuestra un control preciso sobre la arquitectura molecular.

Área de la Ciencia:

Química supramolecular de las moléculas.
Química orgánica es la química orgánica.
Ciencia de los materiales Ciencia de los materiales.

Sus antecedentes:

Las proteínas exhiben estructuras secundarias (hélices, láminas) dictadas por secuencias de aminoácidos.
Los foldameres no naturales son moléculas sintéticas diseñadas para imitar las estructuras de las proteínas y explorar las interacciones no covalentes.

Objetivo del estudio:

Desarrollar una estrategia para crear topologías de plegado distintas en soluciones acuosas.
Para utilizar las propiedades de reconocimiento inherentes de las interacciones donante / aceptador aromático para el diseño de foldamer.

Principales métodos:

Oligómeros sintetizados compuestos por 1,5-dialcoxinaftaleno (Dan) rico en electrones y 1,4,5,8-naftalenetetracarboxilo diimida (Ndi) deficiente en electrones. unidades.
Topologías de plegado investigadas de los trimadores Dan-Ndi-Dan y Dan-Dan-Ndi en soluciones acuosas.
Se empleó la espectroscopia UV-vis y NOESY para analizar las conformaciones moleculares.

Principales resultados:

El trimer Dan-Ndi-Dan adoptó un pliegue plisado en solución.
El isómero constitucional, Dan-Dan-Ndi, adoptó un pliegue intercalativo o de tipo giratorio.
Los análisis espectroscópicos confirmaron las distintas conformaciones adoptadas por los dos isómeros.

Conclusiones:

Demostró la capacidad de diseño de los oligómeros de naftilo plegables.
Destacó la utilidad de las interacciones aromáticas dirigidas para la construcción de complejos conjuntos moleculares en el agua.
Este enfoque ofrece un control preciso sobre la topología del foldamer en entornos acuosos.

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