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Acoplamiento mediado por P450 de fragmentos de indoles para forjar isómeros comunes y no naturales

Hsiao-Ching Lin¹, Travis C McMahon, Ashay Patel

¹Institute of Biological Chemistry, Academia Sinica , Taipei 115, Taiwan.

Journal of the American Chemical Society

|March 11, 2016

Resumen

Los investigadores caracterizaron una enzima P450, CnsC, que crea comunas complejas en los andamios mediante la unión de triptamina y aurantioclavina. Esta enzima forma enlaces clave carbono-carbono y carbono-nitrógeno, lo que permite la síntesis de nuevos compuestos.

Área de la Ciencia:

Síntesis de productos naturales
Enzimología
Química orgánica

Sus antecedentes:

Los alcaloides indólicos diméricos son productos naturales complejos de interés sintético y biosintético significativo.
Comprender su formación es clave para acceder a nuevas estructuras químicas.

Objetivo del estudio:

Caracterización de la monooxigenasa P450 CnsC implicada en la biosíntesis del andamio común.
Para aclarar el mecanismo de CnsC en la catalización de acoplamiento heterodímero y la formación de estereocentros.

Principales métodos:

Caracterización bioquímica del CnsC.
Estudios analógicos de sustrato.
Modelado computacional.
Síntesis enzimática de nuevos compuestos.

Principales resultados:

CnsC cataliza el acoplamiento heterodímero de la triptamina y la aurantioclavina para formar el andamio común.
La enzima media la formación de enlaces carbono-carbono C3-C3' y las subsiguientes formaciones de enlaces aminados.
La síntesis enzimática produjo nuevos compuestos de isocommunesin utilizando precursores modificados de triptamina.

Conclusiones:

CnsC es una enzima clave en la biosíntesis común, controlando las formaciones cruciales de enlaces.
La caracterización de CnsC proporciona información sobre la construcción de andamios complejos de alcaloides indólicos.
Este trabajo permite la síntesis enzimática de derivados de isocommunesin previamente desconocidos.

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