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Ciclos metálicos supramoleculares controlados por el NH quiral
Jinqiao Dong1, Chunxia Tan1, Kang Zhang2
1School of Chemistry and Chemical Technology and State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University , Shanghai 200240, China.
Journal of the American Chemical Society
|January 7, 2017
Resumen
Los investigadores desarrollaron metaciclos quirales fluorescentes para la unión selectiva de moléculas. El aumento de los grupos quirales de NH aumentó la afinidad de unión y la enantioselectividad para las biomoléculas, lo que permitió aplicaciones de detección quirales.
Área de la Ciencia:
- Química supramolecular
- Química de coordinación
- Reconocimiento quiral
Sus antecedentes:
- La discriminación quiral es vital en los sistemas biológicos, pero los métodos sintéticos se enfrentan a desafíos para lograr una alta enantioselectividad.
- La naturaleza utiliza las funcionalidades quirales de NH para el reconocimiento molecular selectivo, inspirando enfoques sintéticos.
Objetivo del estudio:
- Para ensamblar metaciclos quirales fluorescentes para la unión selectiva de moléculas biológicamente activas.
- Investigar el impacto de las funcionalidades quirales del NH en la afinidad de unión y en la enantioselectividad.
- Para desarrollar una plataforma de detección quiral fluorescente.
Principales métodos:
- Síntesis de cíclos metálicos quirales fluorescentes Zn6L6 a partir de complejos de Zn (salaleno) o Zn (salaleno).
- Caracterización mediante difracción de rayos X de un solo cristal y simulaciones moleculares.
- Cálculos químicos cuánticos para aclarar los mecanismos de reconocimiento quiral.
- Espectroscopia de fluorescencia para correlacionar la intensidad de emisión con la composición enantiomérica.
Principales resultados:
- Se ensamblaron con éxito tres metaciclos quirales con un número variable de funcionalidades de NH.
- La afinidad de unión y la enantioselectividad aumentaron con la densidad de grupos quirales de NH en la cavidad del ciclo metálico.
- Los metaciclos demostraron una unión selectiva hacia los ácidos α-hidroxicarboxílicos, los aminoácidos, los productos farmacéuticos y las aminas quirales.
- La intensidad de fluorescencia mostró una relación lineal con el exceso enantiomérico de huéspedes quirales unidos.
Conclusiones:
- Las funcionalidades de NH quiral dentro de las cavidades del ciclo metálico son cruciales para el reconocimiento y la discriminación enantioselectivos.
- El número de grupos quirales de NH influye directamente en el rendimiento de unión y en la enantioselectividad.
- Estos metaciclos sirven como sensores fluorescentes efectivos para las moléculas quirales, con potencial para diseñar sistemas enantioselectivos avanzados.
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