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A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
Published on: September 25, 2017
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La hidroxilación catalizada por el citocromo P450 inicia la formación de éteres en la biosíntesis de la
Jeffrey D Rudolf1, Liao-Bin Dong1, Xiao Zhang1
1Department of Chemistry , The Scripps Research Institute , Jupiter , Florida 33458 , United States.
Journal of the American Chemical Society
|September 15, 2018
Resumen
La platensimicina (PTM) utiliza un enlace de éter único para la potencia. Este estudio revela la enzima PtmO5
Área de la Ciencia:
- Biosíntesis de productos naturales
- Enzimología
- Química orgánica
Sus antecedentes:
- La platensimicina (PTM) y la platencina (PTN) son productos naturales que inhiben las síntases de ácidos grasos.
- La potencia y la selectividad de PTM están vinculadas a una fracción única de éter que no se encuentra en PTN.
- Trabajos anteriores identificaron a PtmT3 como una diterpena sintasa y implicaron a PtmO5 en la formación de éter.
Objetivo del estudio:
- Para aclarar el mecanismo enzimático de la formación de la fracción de éter en la biosíntesis de la platensimicina.
- Caracterizar el papel de la enzima citocromo P450 PtmO5 en este proceso.
Principales métodos:
- Caracterización in vitro de la enzima PtmO5.
- Análisis de la especificidad del sustrato y de los productos de reacción de PtmO5.
- Determinación de la estereoquímica de la hidroxilación y de la formación de éteres.
Principales resultados:
- PtmO5 hidroxila estereoselectivamente la posición C-11 del andamio de ent-kaurano.
- Esta hidroxilación genera un intermediario 11S,16R-diol.
- La fracción de éter en PTM se forma a través de la ciclización de este diol intermedio, con oxígeno de la hidroxilación C-11.
Conclusiones:
- PtmO5 es una enzima clave que cataliza la hidroxilación estereoselectiva C-11 esencial para la fracción de éter de PTM.
- El estudio proporciona una visión mecanicista detallada de una nueva vía de formación de éter en la biosíntesis de productos naturales.
- La comprensión de esta vía puede informar el diseño de nuevos inhibidores de la sintasa de ácidos grasos.
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