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Síntesis de ácidos N-acetilmurámicos funcionalizados para sondear el reciclaje y la biosíntesis de la pared celular

Kristen E DeMeester, Hai Liang, Matthew R Jensen

Journal of the American Chemical Society

|July 10, 2018

Resumen

Los investigadores desarrollaron una síntesis quimioenzimática para bloques de construcción funcionalizados de ácido N-acetilmurámico de uridina (UDP NAM). Este método permite el etiquetado metabólico del peptidoglicano bacteriano (PG) para estudios inmunológicos y microbiológicos.

Área de la Ciencia:

Biosíntesis de las paredes celulares bacterianas
Biología química
Química sintética

Sus antecedentes:

El uridina difosfato N-acetilmuramico (UDP NAM) es esencial para la síntesis de peptidoglicano bacteriano (PG).
La modificación de la NAM UDP permite la incorporación metabólica y la manipulación de la PG.
Los métodos de síntesis y purificación actuales para los derivados de la NAM UDP son difíciles.

Objetivo del estudio:

Desarrollar estrategias de síntesis quimioenzimática robustas para derivados funcionalizados de la UDP NAM.
Para explorar la utilidad de estos derivados para el etiquetado de PG bacteriana.
Permitir el acceso escalable a los MNA del UDP para la investigación fundamental.

Principales métodos:

Síntesis quimioenzimática utilizando una biblioteca de ácido N-acetilmurámico expandido (NAM).
Desarrollo de vías sintéticas para los derivados bioortogonales del ácido 3-láctico NAM.
Prueba de la permisividad enzimática de las enzimas de reciclaje de la pared celular bacteriana (AmgK, MurU).
Etiquetado fluorescente de PG Gram-negativo y Gram-positivo en células enteras utilizando químicas bioortogonales.

Principales resultados:

Síntesis exitosa de varios NAM UDP funcionalizados con 2-N.
Desarrollo de derivados NAM bioortogonales del ácido láctico 3.
Permisibilidad enzimática demostrada de AmgK y MurU a las permutaciones del donante de azúcar.
Etiquetado fluorescente efectivo de la PG bacteriana mediante ligadura con tetrazina y otros métodos bioortogonales.

Conclusiones:

Este estudio proporciona un acceso rápido y escalable a los NAM funcionalizados y los NAM UDP.
Los métodos desarrollados facilitan el etiquetado metabólico de la PG bacteriana.
Estas herramientas se pueden aplicar para investigar el papel de PG en inmunología y microbiología.

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