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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
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Bases moleculares y computacionales para la formación de espirofuranona en la biosíntesis de setosina
Xingxing Wei1, Taro Matsuyama2, Hajime Sato2,3
1Department of Chemistry, City University of Hong Kong, Tat Chee Avenue, Kowloon, Hong Kong SAR, China.
Journal of the American Chemical Society
|October 13, 2021
Resumen
Los investigadores aclararon la biosíntesis del setosusin meroditerpenoide fúngico, revelando un nuevo mecanismo de la enzima citocromo P450 para la formación de espirofuranona. Este descubrimiento arroja luz sobre la producción de productos naturales biológicamente activos.
Área de la Ciencia:
- Biosíntesis de productos naturales
- Metabolismo secundario por hongos
- Catalización de enzimas
Sus antecedentes:
- La fracción 3 ((2H) -furanona está presente en productos naturales bioactivos, incluido el fármaco antifúngico griseofulvin.
- Setosusin (1) es un meroditerpenoide fúngico caracterizado por una estructura distintiva de 3 ((2H) -furanona fusionada con espiro.
- La vía de biosíntesis para la formación de espirofuranona en setosusin se ha mantenido sin investigar desde su aislamiento.
Objetivo del estudio:
- Identificar el grupo de genes biosintéticos para la setosusin (1) en el Aspergillus duricaulis CBS 481.65.
- Elucidar la vía de biosíntesis de la setosusin (1) a través de la expresión heteróloga en Aspergillus oryzae.
- Comprender el mecanismo de reacción subyacente a la formación de espirofuranona.
Principales métodos:
- Identificación del grupo de genes biosintéticos de la setosusin.
- Reconstitución heteróloga de las actividades enzimáticas en Aspergillus oryzae.
- Experimentos de incorporación de isótopos in vivo y in vitro.
- Los cálculos teóricos.
- Mutagénesis dirigida al sitio de la enzima SetF.
Principales resultados:
- Se identificó el clúster de genes biosintéticos para setosusin (1).
- La vía biosintética fue reconstituida en Aspergillus oryzae.
- Se encontró que la enzima del citocromo P450 SetF es crítica para la síntesis de espirofuranona.
- SetF cataliza tanto la epoxidación como un reordenamiento iniciado por la protonación.
- La mutagenesis identificó a Lys303 como un posible residuo catalítico en el SetF.
Conclusiones:
- El estudio aclara la vía de biosíntesis del setosusin meroditerpenoide fúngico (1).
- Se descubrió un nuevo mecanismo que involucra a la enzima citocromo P450 SetF para la formación de espirofuranona.
- Esta investigación proporciona información sobre la biosíntesis de productos naturales complejos y la función de las enzimas.
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