English: The s-triazine herbicide atrazine is a widely used that is persistant in the soil. It is prone to ground and surface water contamination. A range of soil bacteria, including both Gram-negative and Gram-positive strains can degrade atrazine, utilizing it as a nitrogen and carbon source. In this aerobic pathway, which has been studied in most detail in the bacterium Pseudomonas sp. ADP, atrazine is catabolized in three enzymatic steps to cyanurate, which can be further metabolized by ring cleavage to carbon dioxide and ammonia. The first enzyme, encoded by either atzA or trzN (EC 3.8.1.8), converts atrazine to hydroxyatrazine. Two additional hydrolases, encoded by the atzB (EC 3.5.99.3) and atzC (EC 3.5.99.4) genes, continue the process by removing the ethylamine and isopropylamine groups. While some organisms possess all of the required enzymes, other communities degrade atrazine by a community-approach, where different organisms have some of the enzymes, and the intermediates in the pathway are passed between the organisms.

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References

• Boundy-Mills KL, de Souza ML, Mandelbaum RT, Wackett LP, Sadowsky MJ (1997). "The atzB gene of Pseudomonas sp. strain ADP encodes the second enzyme of a novel atrazine degradation pathway." Appl Environ Microbiol 1997;63(3);916-23. PMID: 9055410

• de Souza ML, Wackett LP, Boundy-Mills KL, Mandelbaum RT, Sadowsky MJ (1995). "Cloning, characterization, and expression of a gene region from Pseudomonas sp. strain ADP involved in the dechlorination of atrazine." Appl Environ Microbiol 1995;61(9);3373-8. PMID: 7574646

• de Souza ML, Sadowsky MJ, Wackett LP (1996). "Atrazine chlorohydrolase from Pseudomonas sp. strain ADP: gene sequence, enzyme purification, and protein characterization." J Bacteriol 1996;178(16);4894-900. PMID: 8759853

• de Souza ML, Seffernick J, Martinez B, Sadowsky MJ, Wackett LP (1998). "The atrazine catabolism genes atzABC are widespread and highly conserved." J Bacteriol 1998;180(7);1951-4. PMID: 9537398

• Piutti S, Semon E, Landry D, Hartmann A, Dousset S, Lichtfouse E, Topp E, Soulas G, Martin-Laurent F (2003). "Isolation and characterisation of Nocardioides sp. SP12, an atrazine-degrading bacterial strain possessing the gene trzN from bulk- and maize rhizosphere soil." FEMS Microbiol Lett 221(1);111-7. PMID: 12694918

• Rousseaux S, Hartmann A, Lagacherie B, Piutti S, Andreux F, Soulas G (2003). "Inoculation of an atrazine-degrading strain, Chelatobacter heintzii Cit1, in four different soils: effects of different inoculum densities." Chemosphere 51(7);569-76. PMID: 12615111

• Sadowsky MJ, Tong Z, de Souza M, Wackett LP (1998). "AtzC is a new member of the amidohydrolase protein superfamily and is homologous to other atrazine-metabolizing enzymes." J Bacteriol 1998;180(1);152-8. PMID: 9422605

• Sajjaphan K, Shapir N, Wackett LP, Palmer M, Blackmon B, Tomkins J, Sadowsky MJ (2004). "Arthrobacter aurescens TC1 atrazine catabolism genes trzN, atzB, and atzC are linked on a 160-kilobase region and are functional in Escherichia coli." Appl Environ Microbiol 70(7);4402-7. PMID: 15240330

• Seffernick JL, Johnson G, Sadowsky MJ, Wackett LP (2000). "Substrate specificity of atrazine chlorohydrolase and atrazine-catabolizing bacteria." Appl Environ Microbiol 66(10);4247-52. PMID: 11010866

• Shapir N, Pedersen C, Gil O, Strong L, Seffernick J, Sadowsky MJ, Wackett LP (2006). "TrzN from Arthrobacter aurescens TC1 Is a zinc amidohydrolase." J Bacteriol 188(16);5859-64. PMID: 16885454

• Shapir N, Mongodin EF, Sadowsky MJ, Daugherty SC, Nelson KE, Wackett LP (2007). "Evolution of catabolic pathways: Genomic insights into microbial s-triazine metabolism." J Bacteriol 189(3);674-82. PMID: 17114259

• Smith D, Alvey S, Crowley DE (2005). "Cooperative catabolic pathways within an atrazine-degrading enrichment culture isolated from soil." FEMS Microbiol Ecol 53(2);265-73. PMID: 16329946

• Topp E, Zhu H, Nour SM, Houot S, Lewis M, Cuppels D (2000). "Characterization of an atrazine-degrading Pseudaminobacter sp. isolated from Canadian and French agricultural soils." Appl Environ Microbiol 66(7);2773-82. PMID: 10877767

• Vancov T, Jury K, Van Zwieten L (2005). "Atrazine degradation by encapsulated Rhodococcus erythropolis NI86/21." J Appl Microbiol 99(4);767-75. PMID: 16162227