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Vías paralelas y competitivas para la desaturación del sustrato, la hidroxilación y el reordenamiento radical por la

Harriet L R Cooper¹, Girish Mishra, Xiongyi Huang

¹Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.

Journal of the American Chemical Society

|November 20, 2012

Resumen

La enzima no hemo diirona hidroxilasa AlkB cataliza las reacciones de hidroxilación y desaturación de C-H. Los estudios de isótopos revelan vías paralelas que involucran radicales de carbono, con resultados distintos para las reacciones iniciales C2 y C3.

Área de la Ciencia:

La bioquímica es la bioquímica.
Enzimología Enzimología.
Química orgánica es la química orgánica.

Sus antecedentes:

AlkB es una enzima diirona hidroxilasa no hemo.
La comprensión de los mecanismos de reacción de AlkB es crucial para sus aplicaciones.

Objetivo del estudio:

Para investigar el mecanismo de reacción de AlkB utilizando norcarano como sustrato.
Para dilucidar las vías de hidroxilación y desaturación catalizadas por AlkB.

Principales métodos:

Utilizó norcarano y un análogo deuterado (3,3,4,4-norcarano-d(4) como sustratos de la sonda.
Distribuciones de productos analizados, incluidos los productos de hidroxilación, desaturación y reordenamiento.
Determinación de los efectos cinéticos del isótopo de hidrógeno para diferenciar las vías de reacción.

Principales resultados:

AlkB cataliza la hidroxilación de C2 y C3 y la desaturación del norcarano.
Se observó un efecto significativo del isótopo cinético de hidrógeno (∼20) para la hidroxilación y desaturación de C3.
La deuteración favoreció fuertemente una vía de reordenamiento radical originada en C2.
La desaturación se produce exclusivamente a través de la abstracción de hidrógeno en C3.

Conclusiones:

AlkB reacciona con el norcarano a través de la abstracción inicial de C-H en C2 o C3.
Las vías de hidroxilación y desaturación son paralelas y compiten a través de los radicales de carbono intermedios.
Diferentes radicales intermedios en C2 y C3 conducen a diferentes resultados del producto.

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