Ring cleavage and degradative pathway of cyanuric acid in bacteria

Cook, Alasdair M.; Beilstein, Paul; Grossenbacher, H.; Hütter, Ralf

doi:10.1042/bj2310025

Cited by 88 publications

(69 citation statements)

References 16 publications

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“…1). The product, cyanuric acid, can be metabolized by many different soil bacteria (12,13,18,22). Other commercial s-triazine herbicides vary in the N-alkyl side chain substituents.…”

Section: Discussionmentioning

confidence: 99%

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Purification, Substrate Range, and Metal Center of AtzC: the N -Isopropylammelide Aminohydrolase Involved in Bacterial Atrazine Metabolism

et al. 2002

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The environmental fate of agricultural chemicals is dependent upon their metabolism by microorganisms. s-Triazine herbicides figure prominently in chemical weed control. Atrazine (2-chloro-4-ethylamino-6-isopropylamino-1,3,5-s-triazine) is one of the most widely used s-triazine herbicides for the control of broadleaf weeds in corn (50). Bacteria that metabolize and use s-triazine herbicides as their sole source of nitrogen for growth have only recently been isolated and characterized (9,27,34,46,48,49,52). Metabolism of the s-triazine herbicide atrazine has been extensively studied by using Pseudomonas sp. strain ADP (27) (Fig. 1). Metabolism is initiated via a dechlorination reaction catalyzed by atrazine chlorohydrolase (AtzA) (16,17). In the second reaction of the degradation pathway, AtzB catalyzes the hydrolysis of hydroxyatrazine to yield Nisopropylammelide (8). The third metabolic step utilizes Nisopropylammelide isopropylaminohydrolase (AtzC) to hydrolytically remove N-isopropylamine and generate cyanuric acid (38). Nearly identical genes encoding these enzymes have been found in a wide variety of gram-negative and gram-positive bacteria (9,15,34,36,49) and have been localized to a recently sequenced catabolic plasmid, pADP-1, in Pseudomonas sp. strain ADP (30). While atrazine metabolism is relatively rare among microorganisms, cyanuric acid can be metabolized by many soil bacteria (12,13,18,22). Thus, the advent of bacterial atrazine catabolism is thought to have required the relatively recent evolution of three new enzymes: AtzA, AtzB, and AtzC (41).Interestingly, AtzA, AtzB, and AtzC have all been identified as members of the amidohydrolase protein superfamily (38). Amidohydrolases are distributed throughout the three domains of living organisms: Eubacteria, Archaea, and Eucarya. Members of the superfamily catalyze the hydrolysis of amides or the CON bond of amines (19). Moreover, superfamily members are responsible for key steps in different metabolic pathways, such as purine-pyrimidine metabolism and the degradation of histidine and cytosine (19), and include cytosine deaminase, urease, adenosine deaminase, phosphotriesterase, and ammelide aminohydrolase. These and other amidohydrolase superfamily members have been found to contain mononuclear or binuclear metal centers (19). This has shifted attention to looking for putative metal-coordinating amino acids during sequence analysis of newly identified members of the amidohydrolase superfamily.AtzC shows only modest sequence identity, 27%, to the cytosine deaminase CodA (38). However, sequence analyses of the 35 amino acids that are proposed to reside near or at the four residues which are ligands to a putative metal center show that AtzC and cytosine deaminase have 61% overall sequence identity and 85% sequence similarity. CodA is active with bound

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“…1). The product, cyanuric acid, can be metabolized by many different soil bacteria (12,13,18,22). Other commercial s-triazine herbicides vary in the N-alkyl side chain substituents.…”

Section: Discussionmentioning

confidence: 99%

“…strain ADP (30). While atrazine metabolism is relatively rare among microorganisms, cyanuric acid can be metabolized by many soil bacteria (12,13,18,22). Thus, the advent of bacterial atrazine catabolism is thought to have required the relatively recent evolution of three new enzymes: AtzA, AtzB, and AtzC (41).…”

mentioning

confidence: 99%

Purification, Substrate Range, and Metal Center of AtzC: the N -Isopropylammelide Aminohydrolase Involved in Bacterial Atrazine Metabolism

et al. 2002

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“…strain NRRLB-12227 metabolizes melamine (1,3,5-triazine-2,4,6-triamine) by a six-step pathway through ammeline, ammelide, cyanuric acid, biuret, and urea ( Fig. 1) (3,8,9). Pseudomonas sp.…”

mentioning

confidence: 99%

Cloning and comparison of the DNA encoding ammelide aminohydrolase and cyanuric acid amidohydrolase from three s-triazine-degrading bacterial strains

Eaton

Karns

1991

J Bacteriol

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DNA encoding the catabolism of the s-triazines ammelide and cyanuric acid was cloned from Pseudomonas sp. strain NRRLB-12228 and Klebsiella pneumoniae 99 with, as a probe, a 4.6-kb PstI fragment from a third strain, Pseudomonas sp. strain NRRLB-12227, which also encodes these activities. In strains NRRLB-12228 and 99 the ammelide aminohydrolase (trzC) and cyanuric acid amidohydrolase (trzD) genes are located on identical 4.6-kb PstI fragments which are part of a 12.4-kb DNA segment present in both strains. Strain NRRLB-12227 also carries this 12.4-kb DNA segment, except that a DNA segment of 0.8 to 1.85 kb encoding a third enzyme, ammeline aminohydrolase (trzB), has been inserted next to the ammelide aminohydrolase gene with the accompanying deletion of 1.1 to 2.15 kb of DNA. In addition, the s-triazine catabolic genes are flanked in strain NRRLB-12227 by apparently identical 2.2-kb segments that are not present in the other two strains and that seem to cause rearrangements in adjacent DNA.

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“…It has been reported that a cyanuric acid-mineralizing population frequently occurs in natural environments 3,5,6) . The ring cleavage path- way of cyanuric acid has been also examined 4) . De Souza et al 7) have reported that two deferent bacterial strains in a microbial consortium sequentially catalyze atrazine side-chain removal and ring cleavage, respectively.…”

Section: Mineralization Of Intermediary Metabolite Cyanuric Acidmentioning

confidence: 99%

Role and Behavior of Benthic Microbes Able to Degrade Herbicide Atrazine in Naturally Derived Water/sediment Microcosm.

et al. 2002

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In a simple laboratory microcosm constituted of riverbed sediment and its associated water, rapid degradation of herbicide atrazine mainly to cyanuric acid occurred through microbial degradation. To elucidate the role and behavior of microbes involved in atrazine degradation, comparative microcosms constituted of different sediment/water conditions and constitutions were employed. Fluorescence microscopic observation and direct bacterial count by DAPI (4',6-diamidino-2-phenylindole)-staining and CFU (colony forming unit) count by the plate method were also conducted to supplement the comparative study. As a result, planktonic microbes in the aqueous phase appeared not to be responsible for the initial degradation of atrazine, at least during the present experimental period of 70 days. The sediment was found to be important as a source of degrading microbes. However, once the degradation was initiated, the degrading activity in the aqueous phase was maintained without the sediment. Although CFU in aqueous phase increased with time, this increase in cell number seemed not to reflect the degrading activity. Large, glittering and whole particles, supposed to be microbial cells, were observed by DAPI-staining in the aqueous phase under a microscopic field only when active atrazine-degradation occurred. Therefore, they might be involved in the degrading activity.

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Ring cleavage and degradative pathway of cyanuric acid in bacteria

Cited by 88 publications

References 16 publications

Purification, Substrate Range, and Metal Center of AtzC: the N -Isopropylammelide Aminohydrolase Involved in Bacterial Atrazine Metabolism

Purification, Substrate Range, and Metal Center of AtzC: the N -Isopropylammelide Aminohydrolase Involved in Bacterial Atrazine Metabolism

Cloning and comparison of the DNA encoding ammelide aminohydrolase and cyanuric acid amidohydrolase from three s-triazine-degrading bacterial strains

Role and Behavior of Benthic Microbes Able to Degrade Herbicide Atrazine in Naturally Derived Water/sediment Microcosm.

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