Physical-Chemical Properties and Evaluative Fate Modelling of Phthalate Esters

Cousins, Ian T.; Mackay, Donald; Parkerton, Thomas F.

doi:10.1007/b11463

Cited by 44 publications

(27 citation statements)

References 5 publications

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“…Sewage effluents and sludge have been identified as major routes that bring DEHP into the environment. Several papers analyzed physicochemical properties, degradation pathway, and behavior of DEHP in environmental media (Cousins et al, 2003;Liang et al, 2008;Magdouli et al, 2013;Peterson and Staples, 2003;Staples et al, 1997) or discussed environmental toxicity of DEHP (Kamrin, 2009). However, according to the knowledge of the authors, critical review of the treatment behavior of DEHP in wastewater treatment plants (WWTPs), and quantitative and qualitative comparison of wastewater treatment processes performance in removing DEHP was never performed.…”

Section: Introductionmentioning

confidence: 99%

Occurrence, fate and effects of Di (2-ethylhexyl) phthalate in wastewater treatment plants: A review

Zolfaghari

Drogui

Seyhi

et al. 2014

Environmental Pollution

156

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Section: Introductionmentioning

confidence: 99%

Occurrence, fate and effects of Di (2-ethylhexyl) phthalate in wastewater treatment plants: A review

Zolfaghari

Drogui

Seyhi

et al. 2014

Environmental Pollution

156

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“…Biodegradation of PAEs by microorganisms is considered as the most effective process to eliminate them from the environment (Cousins et al, 2003;Huang et al, 2013;Gao and Wen, 2016). Bacterial PAE degradation is initiated by hydrolysis of the two ester bonds to the corresponding alcohols and phthalate (Liang et al, 2008;Gao and Wen, 2016).…”

Section: Introductionmentioning

confidence: 99%

Enzymes involved in phthalate degradation in sulphate‐reducing bacteria

Geiger

Junghare

Mergelsberg

et al. 2019

Environmental Microbiology

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Summary The complete degradation of the xenobiotic and environmentally harmful phthalate esters is initiated by hydrolysis to alcohols and o‐phthalate (phthalate) by esterases. While further catabolism of phthalate has been studied in aerobic and denitrifying microorganisms, the degradation in obligately anaerobic bacteria has remained obscure. Here, we demonstrate a previously overseen growth of the δ‐proteobacterium Desulfosarcina cetonica with phthalate/sulphate as only carbon and energy sources. Differential proteome and CoA ester pool analyses together with in vitro enzyme assays identified the genes, enzymes and metabolites involved in phthalate uptake and degradation in D. cetonica. Phthalate is initially activated to the short‐lived phthaloyl‐CoA by an ATP‐dependent phthalate CoA ligase (PCL) followed by decarboxylation to the central intermediate benzoyl‐CoA by an UbiD‐like phthaloyl‐CoA decarboxylase (PCD) containing a prenylated flavin cofactor. Genome/metagenome analyses predicted phthalate degradation capacity also in the sulphate‐reducing Desulfobacula toluolica, strain NaphS2, and other δ‐proteobacteria. Our results suggest that phthalate degradation proceeds in all anaerobic bacteria via the labile phthaloyl‐CoA that is captured and decarboxylated by highly abundant PCDs. In contrast, two alternative strategies have been established for the formation of phthaloyl‐CoA, the possibly most unstable CoA ester in biology.

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“…Biodegradation by microorganisms is considered to be the main PAE remediation process (Cousins et al, 2003;Huang et al, 2013), and has predominantly been studied in aerobic cultures (Liang et al, 2008;Gao and Wen, 2016). Degradation is initiated by the hydrolysis of PAE to phthalate and alcohols by esterases.…”

Section: Introductionmentioning

confidence: 99%

An unusual strategy for the anoxic biodegradation of phthalate

et al. 2016

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In the past two decades, the study of oxygen-independent degradation of widely abundant aromatic compounds in anaerobic bacteria has revealed numerous unprecedented enzymatic principles. Surprisingly, the organisms, metabolites and enzymes involved in the degradation of o-phthalate (1,2-dicarboxybenzene), mainly derived from phthalate esters that are annually produced at the million ton scale, are sparsely known. Here, we demonstrate a previously unknown capacity of complete phthalate degradation in established aromatic compound-degrading, denitrifying model organisms of the genera Thauera, Azoarcus and 'Aromatoleum'. Differential proteome analyses revealed phthalate-induced gene clusters involved in uptake and conversion of phthalate to the central intermediate benzoyl-CoA. Enzyme assays provided in vitro evidence for the formation of phthaloyl-CoA by a succinyl-CoA-and phthalate-specific CoA transferase, which is essential for the subsequent oxygen-sensitive decarboxylation to benzoyl-CoA. The extreme instability of the phthaloyl-CoA intermediate requires highly balanced CoA transferase and decarboxylase activities to avoid its cellular accumulation. Phylogenetic analysis revealed phthaloyl-CoA decarboxylase as a novel member of the UbiD-like, (de)carboxylase enzyme family. Homologs of the encoding gene form a phylogenetic cluster and are found in soil, freshwater and marine bacteria; an ongoing global distribution of a possibly only recently evolved degradation pathway is suggested.

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Physical-Chemical Properties and Evaluative Fate Modelling of Phthalate Esters

Cited by 44 publications

References 5 publications

Occurrence, fate and effects of Di (2-ethylhexyl) phthalate in wastewater treatment plants: A review

Occurrence, fate and effects of Di (2-ethylhexyl) phthalate in wastewater treatment plants: A review

Enzymes involved in phthalate degradation in sulphate‐reducing bacteria

An unusual strategy for the anoxic biodegradation of phthalate

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