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La unión reversible del óxido nítrico y la formación de enlaces carbono-carbono en un hemo meso-hidroxilado

Sankar Prasad Rath¹, Richard Koerner, Marilyn M Olmstead

¹Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, USA.

Journal of the American Chemical Society

|September 25, 2003

Resumen

La unión del óxido nítrico a una solución de piridina de octaetiloxoflorina de hierro causa un cambio de color y una dimerización reversibles. Esta reacción forma un nuevo enlace C-C, proporcionando información sobre las vías de degradación del hemo.

Área de la Ciencia:

Química bioorgánica Química bioorgánica.
Coordinación Química de la Coordinación
Química orgánica es la química orgánica.

Sus antecedentes:

Las porfirinas de hierro y los macrociclos relacionados son cruciales en los sistemas biológicos.
Comprender la unión y la reactividad de los ligandos es clave para dilucidar los mecanismos de las metalloenzimas.
La octaetiloxoflorina (OEPO) es un ligando macrocíclico sintético con propiedades electrónicas y estéricas únicas.

Objetivo del estudio:

Para investigar la reacción de (py) 2Fe ((OEPO) con óxido nítrico (NO) en condiciones anaerobias.
Para caracterizar el adducto NO resultante y entender sus características estructurales y electrónicas.
Explorar las implicaciones de la estructura observada para los mecanismos de degradación del hemo.

Principales métodos:

Seguimiento espectroscópico (UV-Vis, 1H RMN) de la reacción.
Aislamiento y caracterización del producto por cristalografía de rayos X.
Análisis de la distorsión del ligando y la proximidad de los sitios reactivos.

Principales resultados:

La exposición al NO dio lugar a un cambio de color de verde a marrón rojo y la formación de {(py)
Se encontró que la reacción era reversible a través de la espectroscopia de RMN de 1H.
La cristalografía de rayos X reveló la dimerización a través de un enlace C-C entre los mesocarbonos, con el ligando NO posicionado cerca de la posición meso oxigenada del macrociclo.

Conclusiones:

La unión de NO induce la dimerización y los cambios estructurales en el complejo de octaetiloxoflorina de hierro.
La estructura observada proporciona un modelo para las etapas iniciales de la degradación del hemo que involucra el ataque de oxígeno.
El macrociclo enrollado y la proximidad del NO al mesocarbono oxigenado son características clave para comprender la reactividad del hemo.

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