Bacterial Nitration of 4-Chlorobiphenyl

In the course of a study dealing with the biodegradation of 4-chlorobiphenyl by strain B-206, we noticed that the gram-negative bacterium accumulated different metabolic intermediates depending on the nitrogen source of the medium. Hence, in the presence of nitrate, strain B-206 produced four compounds which were identified as 2- and 4-hydroxy-4′-chlorobiphenyl and 2- and 4-hydroxy-mononitro-4′-chlorobiphenyl. The accumulation of these compounds in the culture medium indicated the presence of a monooxygenase in strain B-206 leading to the production of arene oxide intermediates. The possible transformation of 4-chlorobiphenyl to an arene oxide by this bacterial strain is a matter of concern because of the high reactivity of these arene oxides with biological material.