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Transferencia de quiralidad estereodivergente por control no covalente de enlaces disulfuro

Qi Zhang^1,2, Stefano Crespi², Ryojun Toyoda²

¹Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China.

Journal of the American Chemical Society

|February 4, 2022

Resumen

Los enlaces de hidrógeno controlan la quiralidad del disulfuro en proteínas y sistemas autoensamblados. Este estudio revela cómo estos enlaces permiten la transferencia de quiralidad estereodivergente, desbloqueando el control estereocímico dinámico.

Área de la Ciencia:

La bioquímica
Química supramolecular
Química orgánica

Sus antecedentes:

La estereoquímica dinámica es crucial para la función de las proteínas y el ensamblaje supramolecular.
Los enlaces disulfuro en las proteínas suelen mostrar un comportamiento estereodivergente, pero el mecanismo de transferencia de quiralidad no se entiende bien.

Objetivo del estudio:

Investigar el papel de los enlaces de hidrógeno en el control de la quiralidad de los enlaces disulfuro.
Elucidar los mecanismos de transferencia de quiralidad estereodivergente mediada por enlaces de hidrógeno.

Principales métodos:

Investigación de la formación de enlaces de hidrógeno (S-S··H-N y C=O··H-N) en solución y estado sólido.
Se analizó la transferencia de quiralidad de los bloques de construcción de aminoácidos homoquirales.

Principales resultados:

Los enlaces de hidrógeno son esenciales para controlar la quiralidad del disulfuro.
Los enlaces de hidrógeno S-S-H-N facilitan la transferencia de quiralidad intramolecular en la solución.
Los enlaces de hidrógeno C=O·H-N impulsan la transferencia de quiralidad supramolecular, formando arquitecturas helicoidales autoensambladas.

Conclusiones:

Los enlaces de hidrógeno son mediadores clave de la transferencia de quiralidad estereodivergente en sistemas que contienen disulfuro.
Las interacciones no covalentes permiten el acceso a diversos espacios estereoquímicos dinámicos.
Comprender estos principios es vital para la ingeniería de proteínas y el diseño de nuevos materiales de autoensamblaje.

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