Streptomyces scabies produces 5-nitroanthranilate (5NAA), but its physiological role is not known (RR King, CH Lawrence and LA Calhoun, 1998, Phytochemistry, 49: 1265-1267). Synthetic 5NAA is used as the starting material for other nitroaromatic compounds and dyes (Baxter and Bennion, May 1956, U.S. patent 749,320.23).
Bradyrhizobium JS329 can use 5NAA as its sole source of carbon, nitrogen, and energy. The degradation pathway involves an unusual hydrolytic removal of the amino group to form 5-nitrosalicylate, followed by ring cleavage without removal of the nitro group, proposed to produce 4-nitro-6-oxohepta-2,4-dienodioate (Qu and Spain, 2010).
The following is a text-format 5-nitroanthranilate pathway map. An organism which can initiate the pathway is given, but other organisms may also carry out later steps. Follow the links for more information on compounds or reactions. This map is also available in graphic (10k) format.
5-Nitroanthranilate Bradyrhizobium sp. JS329 | | | 5-nitroanthanilate | aminohydrolase | v 5-Nitrosalicylate | | | 5-nitrosalicylate | 1,2-dioxygenase | v [4-Nitro-6-oxohepta-] [2,4-dienedioate]
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