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Biosíntesis eficiente de poliquetidas de hongos que contienen el sistema de anillos de dioxabiciclo-octano

Xu-Ming Mao¹, Zha-Jun Zhan², Matthew N Grayson

¹College of Life Sciences, Zhejiang University , Hangzhou 310058, China.

Journal of the American Chemical Society

|September 5, 2015

Resumen

Las aurovertinas, policetidas fúngicas que inhiben la adenosina trifosfato sintasa, se sintetizan a través de una vía concisa. Cuatro enzimas convierten un precursor de polieno en el complejo andamio dioxabiciclo [3.2.1] octano, lo que demuestra una eficiente biosíntesis de productos naturales.

Área de la Ciencia:

La bioquímica
Biosíntesis de productos naturales
Micología

Sus antecedentes:

Las aurovertinas son policetidas fúngicas conocidas por su potente inhibición de la adenosina trifosfato sintasa.
Se cree que su característico anillo de 2,6-dioxabiciclo [3.2.1] octaño surge de un precursor de polieno a través de la oxidación y la apertura de epóxido.
La comprensión de la vía biosintética es clave para elucidar la formación de productos naturales complejos.

Objetivo del estudio:

Identificar el conjunto mínimo de enzimas requerido para la biosíntesis de aurovertina E.
Para aclarar las transformaciones bioquímicas involucradas en la generación del andamio de 2,6-dioxabiciclo [3.2.1].
Demostrar la eficiencia de las vías de biosíntesis de hongos en la creación de estructuras moleculares complejas.

Principales métodos:

Identificación y caracterización de las enzimas.
Análisis de los productos de la poliquetida sintasa.
Investigación de las actividades de la metiltransferasa, la monooxigenasa dependiente de la flavina y la epoxida hidrolasa.
Identificación de los productos intermedios de biosíntesis mediante análisis químico.

Principales resultados:

Se encontró que solo cuatro enzimas eran esenciales para la producción de aurovertina E.
El núcleo de la policetida sintasa genera un precursor de polieno α-pirona.
Una mono-oxigenasa dependiente de la flavina y la hidrolasa epóxica modifican iterativamente el precursor en el andamio cíclico.
Se identificó un polieno tetrahidrofuranilo como el primer intermediario estable, sometido a la epoxidación y la apertura del anillo.

Conclusiones:

La biosíntesis de hongos emplea una maquinaria enzimática muy concisa para construir andamios complejos de aurovertina.
La vía identificada pone de relieve estrategias eficientes para generar productos de éter cíclico a partir de precursores de polieno.
Este estudio proporciona información importante sobre los mecanismos de la biosíntesis de productos naturales de hongos.

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