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Published on: November 8, 2010
Reconocimiento quiral de complejos metálicos helicoidales mediante ciclodextrinas modificadas
1Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Kyotanabe, Kyoto 610-0321, Japan.
Journal of the American Chemical Society
|October 25, 2001
Resumen
Los complejos metálicos quirales como el rutenio ((II) tris ((1,10-fenantrolina) son reconocidos por las ciclodextrinas modificadas. Las ciclodextrinas específicas, heptakis ((6-carboxymethylthio-6-deoxy) -beta-cyclodextrin y hexakis ((2,3,6-tri-O-methyl) -alfa-cyclodextrin, muestran una unión enantioselectiva, lo que indica capacidades de reconocimiento quiral.
Área de la Ciencia:
- Coordinación Química de la Coordinación
- Química supramolecular de las moléculas.
- Reconocimiento Quiral de Reconocimiento Quiral
Sus antecedentes:
- La quiralidad es una propiedad fundamental en química y biología.
- Las ciclodextrinas son ampliamente utilizadas como moléculas huésped en la química supramolecular.
- Los complejos metálicos, particularmente aquellos con estructuras quirales, son importantes en varias aplicaciones.
Objetivo del estudio:
- Para investigar el reconocimiento quiral de los complejos metálicos M(fen) 3(n+) por ciclodextrinas modificadas.
- Determinar las constantes de unión y los parámetros termodinámicos para la complejidad de los enantiómeros.
- Para aclarar los mecanismos y las fuerzas motrices detrás de la unión enantioselectiva.
Principales métodos:
- La titulación espectrofotométrica para determinar las constantes de unión (K).
- Calorimetría de titulación isotérmica (ITC) para estudiar los parámetros termodinámicos (cambios de entropía y entalpía).
- Uso de disolvente D2O y amortiguador de fosfato en pD 7.0 para experimentos.
Principales resultados:
- Heptakis ((6-carboximetiltio-6-deoxy) -beta-ciclodextrina (por-CO2 ((-) -beta-CD) mostró una unión preferente con el delta-rufen) 3 2 +).
- Hexakis ((2,3,6-tri-O-metil) -alfa-ciclodextrina (TMe-alfa-CD) exhibió una unión enantioselectiva hacia Ru (((fen) 3 ((2+) y Ru ((bpy) 3 ((2+)).
- Los efectos de Pfeiffer se observaron para los complejos Fe (II), Co (II) y Zn (II) con per-CO2 (II) -beta-CD, lo que indica una inducción quiral.
Conclusiones:
- Las ciclodextrinas modificadas pueden reconocer y discriminar efectivamente entre los enantiómeros de los complejos metálicos quirales.
- El mecanismo de unión implica una combinación de interacciones de Coulomb, la inclusión en la cavidad del huésped y las fuerzas de van der Waals.
- Las interacciones específicas están influenciadas por la quiralidad de la molécula huésped y las características estructurales del huésped ciclodextrina.
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