Bacterial Decarboxylation of
            <i>o</i>
            -Phthalic Acids

Taylor, Barrie F.; Ribbons, Douglas W.

doi:10.1128/aem.46.6.1276-1281.1983

Cited by 29 publications

(18 citation statements)

References 25 publications

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“…As proposed for denitrifying bacteria (21,22,30), the initial step in the degradation of phthalate isomers is suggested to be decarboxylation to benzoate because (i) all the phthalateisomer-grown cultures were capable of benzoate degradation without a lag phase and (ii) small amounts of benzoate accumulated in phthalate-isomer-degrading cultures incubated with the methanogenic inhibitor BES.…”

Section: Discussionmentioning

confidence: 99%

“…Another explanation for the postulated energetic inefficiency can be found in the decarboxylation of the phthalates to benzoate (or their CoA analogues). Taylor and Ribbons (30) suggested that decarboxylation of phthalate may proceed after the initial partial reduction of the aromatic ring (in a one-or two-electron mechanism), followed by oxidative decarboxylation. The initial reduction of the aromatic ring is endergonic and requires the investment of energy in the form of ATP (3).…”

Section: Discussionmentioning

confidence: 99%

“…The metabolic pathway for anoxic degradation of phthalic acid isomers in a denitrifying Pseudomonas sp. in-volves initial activation of ortho-phthalate by coenzyme A (CoA), probably followed by decarboxylation resulting in the formation of benzoyl CoA (21,22,30). No experimental evidence is available about the exact location of the decarboxylation in the degradation pathway, but the current view is that benzoyl-CoA is the only central intermediate in the anoxic mineralization of a large range of aromatic compounds (besides aromatic compounds with at least two phenolic functional groups).…”

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confidence: 99%

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Anaerobic Degradation of Phthalate Isomers by Methanogenic Consortia

Kleerebezem¹,

Pol²,

Lettinga³

1999

Appl Environ Microbiol

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Three methanogenic enrichment cultures, grown onortho-phthalate, iso-phthalate, or terephthalate were obtained from digested sewage sludge or methanogenic granular sludge. Cultures grown on one of the phthalate isomers were not capable of degrading the other phthalate isomers. All three cultures had the ability to degrade benzoate. Maximum specific growth rates (μS max) and biomass yields (YXtot S) of the mixed cultures were determined by using both the phthalate isomers and benzoate as substrates. Comparable values for these parameters were found for all three cultures. Values for μS max and YXtot S were higher for growth on benzoate compared to the phthalate isomers. Based on measured and estimated values for the microbial yield of the methanogens in the mixed culture, specific yields for the phthalate and benzoate fermenting organisms were calculated. A kinetic model, involving three microbial species, was developed to predict intermediate acetate and hydrogen accumulation and the final production of methane. Values for the ratio of the concentrations of methanogenic organisms, versus the phthalate isomer and benzoate fermenting organisms, and apparent half-saturation constants (KS) for the methanogens were calculated. By using this combination of measured and estimated parameter values, a reasonable description of intermediate accumulation and methane formation was obtained, with the initial concentration of phthalate fermenting organisms being the only variable. The energetic efficiency for growth of the fermenting organisms on the phthalate isomers was calculated to be significantly smaller than for growth on benzoate.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

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Anaerobic Degradation of Phthalate Isomers by Methanogenic Consortia

Kleerebezem¹,

Pol²,

Lettinga³

1999

Appl Environ Microbiol

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“…It was soon postulated that in anaerobic bacteria PA is decarboxylated to benzoate followed by thioesterification, e.g. by an ATP‐dependent benzoate CoA ligase (Eaton and Ribbons, ; Taylor and Ribbons, ). However, decarboxylation of any of the three phthalate isomers to benzoate would afford an extremely unfavourable dianionic intermediate.…”

Section: Introductionmentioning

confidence: 99%

Microbial degradation of phthalates: biochemistry and environmental implications

Boll

Geiger

Junghare

et al. 2019

Environ Microbiol Rep

122

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Summary The environmentally relevant xenobiotic esters of phthalic acid (PA), isophthalic acid (IPA) and terephthalic acid (TPA) are produced on a million ton scale annually and are predominantly used as plastic polymers or plasticizers. Degradation by microorganisms is considered as the most effective means of their elimination from the environment and proceeds via hydrolysis to the corresponding PA isomers and alcohols under oxic and anoxic conditions. Further degradation of PA, IPA and TPA differs fundamentally between anaerobic and aerobic microorganisms. The latter introduce hydroxyl functionalities by dioxygenases to facilitate subsequent decarboxylation by either aromatizing dehydrogenases or cofactor‐free decarboxylases. In contrast, anaerobic bacteria activate the PA isomers to the respective thioesters using CoA ligases or CoA transferases followed by decarboxylation to the central intermediate benzoyl‐CoA. Decarboxylases acting on the three PA CoA thioesters belong to the UbiD enzyme family that harbour a prenylated flavin mononucleotide (FMN) cofactor to achieve the mechanistically challenging decarboxylation. Capture of the extremely instable PA‐CoA intermediate is accomplished by a massive overproduction of phthaloyl‐CoA decarboxylase and a balanced production of PA‐CoA forming/decarboxylating enzymes. The strategy of anaerobic phthalate degradation probably represents a snapshot of an ongoing evolution of a xenobiotic degradation pathway via a short‐lived reaction intermediate.

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“…At anoxic habitats, complete oxidation of phthalate to CO 2 is considered a rate-limiting step of PAE degradation (Gao and Wen, 2016). The decarboxylation of phthalate to benzoate, either directly or after activation to a CoA thioester, has been proposed more than three decades ago (Taylor and Ribbons, 1983;Nozawa and Maruyama, 1988;Kleerebezem, 1999). However, the genes and enzymes involved in oxygen-independent degradation of phthalate were only recently elucidated in studies with denitrifying, phthalate-degrading Thauera, Azoarcus and Aromatoleum strains (Junghare et al, 2016;Ebenau-Jehle et al, 2017).…”

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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Bacterial Decarboxylation of o -Phthalic Acids

Cited by 29 publications

References 25 publications

Anaerobic Degradation of Phthalate Isomers by Methanogenic Consortia

Anaerobic Degradation of Phthalate Isomers by Methanogenic Consortia

Microbial degradation of phthalates: biochemistry and environmental implications

Enzymes involved in phthalate degradation in sulphate‐reducing bacteria

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