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Base enzimática de la prenilación del péptido ribosomal en las cianobacterias
John A McIntosh1, Mohamed S Donia, Satish K Nair
1Department of Medicinal Chemistry, University of Utah, Salt Lake City, Utah 84112, United States.
Journal of the American Chemical Society
|July 20, 2011
Resumen
Los investigadores identificaron LynF, una enzima preniltransferasa, responsable de modificar los péptidos cíclicos llamados cianobactinas. Este descubrimiento revela una nueva vía para la biosíntesis de productos naturales que implica la prenilación de péptidos maduros y un mecanismo de reordenamiento Claisen.
Área de la Ciencia:
- La bioquímica es la bioquímica.
- Biosíntesis de Productos Naturales de Productos Naturales
- Enzimología Enzimología.
Sus antecedentes:
- Los mecanismos enzimáticos para la prenilación de los productos naturales del péptido ribosomal siguen siendo en gran medida no caracterizados.
- La prenilación es una modificación post-traducional clave en la biosíntesis de muchos productos naturales bioactivos.
Objetivo del estudio:
- Para dilucidar la base enzimática de la prenilación del péptido ribosómico.
- Para caracterizar la preniltransferasa LynF y su papel en la biosíntesis de la cianobactina.
- Investigar el mecanismo de la C-prenilación en productos naturales.
Principales métodos:
- Caracterización de la enzima de LynF.
- Análisis de la prenilación de los residuos de tirosina, serina y treonina en péptidos cíclicos.
- Investigación del reordenamiento Claisen de los derivados de tirosina prenilados.
Principales resultados:
- Se caracterizó LynF, una nueva preniltransferasa de la familia de enzimas TruF.
- LynF realiza la O-prenilación inversa de la tirosina en péptidos macrocíclicos maduros, independientemente de las secuencias de líder.
- La tirosina O-prenilada inversa se somete a una reorganización de Claisen para producir productos C-prenilados, lo que demuestra una nueva ruta biosintética.
Conclusiones:
- La familia de enzimas TruF prenila los péptidos cíclicos maduros, desafiando el modelo convencional que requiere secuencias de líder para modificaciones post-traducionales.
- Un mecanismo de reordenamiento de Claisen impulsa la C-prenilación fenólica en la biosíntesis de productos naturales, una vía previamente sólo anticipada químicamente.
- Este estudio proporciona nuevos conocimientos sobre la biosíntesis de productos naturales prenilados y amplía nuestra comprensión de la función de las enzimas.
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