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Biosíntesis enantioselectiva de las aurantinas (+) y (-)
Shinji Kishimoto1, Tsubasa Tamura1, Takumi Okamoto1
1Department of Pharmaceutical Sciences, University of Shizuoka, Shizuoka 422-8526, Japan.
Journal of the American Chemical Society
|March 18, 2025
Resumen
Las cepas fúngicas de Aspergillus lentulus producen enantiómeros del producto natural aurantina a través de distintas vías de biosíntesis. Este estudio revela la biosíntesis única de aminoácidos que contienen nitrilo y la producción de productos naturales enantioméricos en hongos.
Área de la Ciencia:
- * Micología y química de los productos naturales
- * Bioquímica y Biología Molecular
Sus antecedentes:
- * Los productos naturales bioactivos (PN) suelen estar controlados estereocímicamente durante la biosíntesis.
- * Los enantiómeros (isómeros de imagen especular) se encuentran raramente entre los metabolitos fúngicos debido a la estereospecificidad enzimática.
- * La aurantina es un NP fúngico que contiene un grupo nitrilo, cuya biosíntesis no se había caracterizado anteriormente.
Objetivo del estudio:
- * Investigar la biosíntesis de enantiómeros de aurantina producidos por diferentes cepas de Aspergillus lentulus.
- * Identificar los genes y enzimas responsables de la producción de los isómeros (-) y (+) de la aurantina.
- * Para aclarar el mecanismo de la biosíntesis de aminoácidos que contienen nitrilo en los hongos.
Principales métodos:
- * Análisis transcriptómico para identificar los genes relevantes.
- * Deleción de genes y experimentos de expresión heteróloga para confirmar la función de los genes.
- * Pruebas bioquímicas para caracterizar la actividad enzimática.
Principales resultados:
- * Se identificaron dos distintas sintetasas de péptidos no ribosómicos (NRPS), NitA y NitC, responsables de la síntesis de (-) y (+) -aurantina, respectivamente.
- * Descubrió que NitC posee un dominio de epimerización, lo que explica la producción del par enantiomérico.
- * NitB caracterizado, una enzima similar a la argininosuccinato sintetasa, que cataliza la biosíntesis del aminoácido que contiene nitrilo l-γ-cianohomoalanina de la l-glutamina.
Conclusiones:
- * Diferentes cepas de Aspergillus lentulus producen enantiómeros de aurantina a través de distintas enzimas NRPS (NitA y NitC).
- * La presencia de un dominio de epimerización en NitC es clave para generar el par enantiomérico.
- * Se esclareció una nueva vía para la biosíntesis de aminoácidos que contienen nitrilo que involucra a NitB.
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