Anaerobic Biotransformation of N-oxide Containing Aromatic Heterocycles by Bovine Ruminal Fluid

Biotransformação Anaeróbia de Heterociclos Aromáticos Contendo N-óxido por Líquido Ruminal de Bovinos

Cerecetto González, María Victoria - Díaz Viraqué, Florencia - Irazoqui, Ignacio - Rodríguez, Alfonso - Cajarville, Cecilia - Repetto, José Luis - Lavaggi, María Laura - González, Mercedes - Cerecetto, Hugo

Resumen:

Microorganisms of bovine rumen fluid have been studied as biocatalysts for the reduction of different N-oxide containing aromatic heterocycles, i.e. quinoxaline N1,N4-dioxide, phenazine N5,N10-dioxide, indazole N1-oxide, benzofuroxan and furoxan. In anaerobiosis, the microorganisms biocatalyzed the reduction of some N-oxides, quinoxaline and phenazine dioxides, to yield the corresponding heterocycle while in the case of benzofuroxans the heterocycle-opening, o-nitroaniline was generated as the unique product. Contrarily, the furoxan was not biotransformed in the studied conditions. The indazole N1-oxide was biotransformed very slowly and incompletely in the corresponding indazole. Only one of the studied indazole N1-oxide derivative was completely converted to a new compound, different to the expected reduced indazole. For that, a semi-preparative scale biotransformation was performed and the new product was spectroscopically identified.

Detalles Bibliográficos
2013
BOVINOS
FLUIDO DEL RUMEN
ANAEROBIOSIS
MICROORGANISMOS
Español
Universidad de la República
COLIBRI
https://hdl.handle.net/20.500.12008/51545
http://dx.doi.org/10.5935/1984-6835.20130082
Acceso abierto
Licencia Creative Commons Atribución (CC - By 4.0)