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Origen biosintético del anillo de éter en la platensimicina

Jeffrey D Rudolf¹, Liao-Bin Dong¹, Karina Manoogian¹

¹Department of Chemistry, ‡Department of Molecular Therapeutics, and §Natural Products Library Initiative at The Scripps Research Institute, The Scripps Research Institute , Jupiter, Florida 33458, United States.

Journal of the American Chemical Society

|December 15, 2016

Resumen

Los investigadores identificaron dos genes clave, ptmT3 y ptmO5, que controlan las diferentes vías de biosíntesis para los productos naturales de platensimicina (PTM) y platencina (PTN). Estos hallazgos revelan elementos estructurales cruciales para el PTM

Área de la Ciencia:

Biosíntesis de productos naturales
Metabolismo secundario microbiano
Catalización de enzimas

Sus antecedentes:

La platensimicina (PTM) y la platencina (PTN) son diterpenoides bacterianos que inhiben las síntases de ácidos grasos.
El PTM inhibe selectivamente el FabF/FabB, mientras que el PTN inhibe el FabF/FabB y el FabH.
Trabajos anteriores identificaron el papel de la cinta PTM en la partición de la biosíntesis de cetolidos.

Objetivo del estudio:

Investigar el papel de la cinta PTM en la divergencia de la biosíntesis de cetólidos diterpenoides.
Identificar los genes específicos responsables de las diferencias de biosíntesis de PTM y PTN.
Elucidar la función de PtmT3 y PtmO5 en la vía PTM/PTN.

Principales métodos:

Construcción de sistemas de producción de diterpenos en E. coli.
Manipulación genética de Streptomyces platensis SB12029 (productor doble de PTM y PTN).
Inactivación de genes (ptmO5) y análisis de congéneres acumulados de PTM/PTN.

Principales resultados:

Se identificaron ptmT3 y ptmO5 como genes clave en la divergencia biosintética PTM/PTN.
PtmT3 es una nueva diterpena sintasa de tipo I bacteriana ((16R) -ent-kauran-16-ol sintasa).
PtmO5 (citocromo P450) probablemente forma el anillo de éter PTM; su inactivación produjo nuevos congéneres.

Conclusiones:

La cinta PTM, específicamente PtmT3 y PtmO5, dicta la biosíntesis divergente de los cetólidos PTM y PTN.
El anillo de éter 11S, 16S, o estereoquímica C-16, es crítico para la actividad antibacteriana de PTM.
Descubrimiento de una nueva diterpena sintasa bacteriana y conocimientos sobre la biosíntesis PTM/PTN y las relaciones estructura-actividad.

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