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Síntesis de la toxina del hongo de la muerte α-amanitina
Kaveh Matinkhoo1, Alla Pryyma1, Mihajlo Todorovic1
1Chemistry Department , The University of British Columbia , 2036 Main Mall , Vancouver , British Columbia V6T-1Z1 , Canada.
Journal of the American Chemical Society
|March 22, 2018
Resumen
Los científicos sintetizaron la α-amanitina, una potente toxina del hongo de la muerte, superando los principales desafíos químicos. Este avance ofrece una alternativa sostenible a la extracción de hongos para posibles terapias contra el cáncer.
Área de la Ciencia:
- Química orgánica
- Química medicinal
- La bioquímica
Sus antecedentes:
- La α-amanitina es un octapeptido altamente tóxico de la Amanita phalloides.
- Funciona como un potente inhibidor de la ARN polimerasa II, causando toxicidad en las células eucariotas.
- La α-amanitina se muestra prometedora como una carga útil para los conjugados de anticuerpos y fármacos en el tratamiento del cáncer.
Objetivo del estudio:
- Desarrollar una vía sintética para la α-amanitina.
- Para abordar los desafíos en la síntesis de la estructura compleja de la α-amanitina.
- Proporcionar una fuente fiable de α-amanitina independiente del aislamiento natural.
Principales métodos:
- Síntesis total de la α-amanitina.
- Síntesis enantioselectiva de (2 S,3 R,4 R) -4,5-dihidroxi-isoleucina.
- Diastereoselectividad de la sulfoxidación para la construcción de puentes de triptationina sulfoxida.
Principales resultados:
- Síntesis exitosa de la α-amanitina.
- Superó los desafíos para formar el único puente de sulfóxido.
- Establecer un control enantioselectivo y diastereoselectivo en las etapas clave.
Conclusiones:
- Se ha establecido una vía sintética viable para la α-amanitina.
- Esta síntesis ofrece una alternativa a las fuentes naturales.
- Permite una mayor exploración de la α-amanitina en aplicaciones terapéuticas.
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