N-acetyl-o-toluidine Pathway Map

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This pathway was contributed by Debora Käser, Eawag.

N-acetyl-o-toluidine is known for its carcinogenic effect on humans. N-acetyl-o-toluidine can get formed by the metabolism of o-Toluidine in humans via N-acetyltaion. This mechanism is the primary detoxification mechanism in humans for aromatic amines. The common use of o-Toluidine is in the preparation of methyl ethyl aniline, which is an intermediate during the production of certain herbicides. Further it is used during the synthesis of rubber chemicals, dyes and pigments, fungicides as well as pharmaceuticals (Caroline English et al., 2012).

In laboratory batch experiments with activated sludge from a membrane bioreactor, the main transformation product observed was the product of enzymatic hydrolysis at the amide functional group ( Helbling et al., 2010). In earlier experiments the degradation of N-acetyl-o-toluidine was examined in Norcardia Globerula. Further transformation products were found to be 4-hydroxy-o-toluidine through a hydroxylation of o-toluidine and 4-hydroxy-N-acetyl-o-toluidine through an acetylation of 4-hydroxy-o-toluidine (Yoshioka et al., 1991).

The following is a text-format N-acetyl-o-toluidine map. Mixed bacterial cultures from activated sludge treatment or Norcardia Globerula can initiate the pathway. Follow the links for more information on compounds or reactions. This map is also available in graphic (5k) format.

                   N-acetyl-o-toluidine
        	   Aerobic mixed culture
              from activated sludge treatment 
		   and Norcardia Globerula
                 	    |
                 	    | aryl                          
                 	    | acylamidase 
                 	    |
                 	    v
                       o-Toluidine
			    |
			    | o-toluidine
			    | hydroxylase
			    |
			    v
		  4-Hydroxy-o-toluidine
			    |
			    | 4'-Hydroxy-N-acetyl-o-toluidine
			    | N-acetyltransferase
			    |
			    v
	     4'-Hydroxy-N-acetyl-o-toluidine

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Page Author(s): Debora Käser

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