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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. DOI: 10.5935/1984-6835.20130082Micro-organismos do fluido ruminal de bovinos foram estudados como biocatalizadores para a redução de diferentes heterociclos aromáticos contendo N-óxido, isto é, quinoxalina N1,N4-dióxido, fenazina N5,N10-dióxido, indazol N1-óxido, benzofuroxano e furoxano. Em anaerobiose, os micro-organismos biocatalisam a redução de alguns N-óxidos, dióxidos de quinoxalina e fenazina para se obter os heterociclos correspondentes, enquanto no caso do heterociclo benzofuroxano, ocorre abertura do anel, gerando a o-nitroanilina como único produto. Ao contrário, o furoxano não foi biotransformado nas condições estudadas. O indazol N1-óxido foi biotransformado lenta e incompletamente ao indazol correspondente. Exceção foi observada apenas para um dos N1-óxidos de indazol, que foi completamente convertido a um composto novo, diferente do indazol reduzido esperado. A biotransformação em escala semi-preparativa foi realizada e o novo produto obtido e identificado por métodos espectroscópicos. DOI: 10.5935/1984-6835.2013008

Anaerobic Biotransformation ofN-oxide Containing Aromatic Heterocycles by Bovine Ruminal Fluid