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Síntesis eficiente y revisión estereoquímica de la coibamida A

Guiyang Yao^1,2, Zhengyin Pan¹, Chunlei Wu¹

¹Guangdong Key Laboratory of Nanomedicine, Institute of Biomedicine and Biotechnology, Shenzhen Institutes of Advanced Technology, Chinese Academy of Sciences , Shenzhen, Guangdong, 518055, P. R. China.

Journal of the American Chemical Society

|October 16, 2015

Resumen

Los investigadores desarrollaron una nueva síntesis de fase sólida para los ciclodepsipéptidos N-metilados, lo que permite la creación de derivados de coibamida A. Este método condujo a la primera síntesis total y estereoquímica revisada de la coibamida A.

Área de la Ciencia:

Química de los productos naturales marinos
Química orgánica sintética
Química medicinal

Sus antecedentes:

La coibamida A es un potente ciclodepsipéptido antiproliferativo de las cianobacterias marinas.
Comprender sus relaciones estructura-actividad es crucial para el desarrollo de fármacos.

Objetivo del estudio:

Desarrollar una síntesis de fase sólida eficiente para los ciclodepsiptidos N-metilados.
Para generar derivados de la coibamida A para estudios de relación estructura-actividad (SAR).
Para lograr la primera síntesis total de coibamida A.

Principales métodos:

Desarrollo de una nueva estrategia de fase sólida para el ensamblaje de cíclopeptidos altamente N-metilados.
Aplicación de la estrategia sintética a la coibamida A y sus derivados.
Revisión de las asignaciones estereoquímicas basadas en resultados sintéticos.

Principales resultados:

Se estableció una síntesis de fase sólida eficiente para los ciclodepsiptidos N-metilados.
Se logró por primera vez la síntesis total de coibamida A.
Se revisaron dos asignaciones estereoquímicas de la coibamida A, aclarando su estructura.

Conclusiones:

La estrategia de fase sólida desarrollada es valiosa para sintetizar derivados de coibamida A y compuestos relacionados.
La estereoquímica revisada y la síntesis total proporcionan una base para futuros estudios de SAR y esfuerzos de descubrimiento de fármacos.
Este trabajo promueve la accesibilidad sintética de productos naturales marinos complejos.

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