CO2–H2-dependent anaerobic biotransformation of phthalic acid isomers in sediment slurries

Liu, S.-M.; Chi, Wanqing

doi:10.1016/s0045-6535(03)00326-6

Cited by 25 publications

(7 citation statements)

References 28 publications

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“…Until recently, knowledge of anaerobic degradation of PA in obligately anaerobic bacteria was restricted to a few studies with sediment slurries and enrichment cultures (Kleerebezem et al ., ; Kleerebezem et al ., ; Liu and Chi, ; Liu et al ., ; Liu et al ., ). Further, a Pelotomaculum isopthalicum species has been described that grows with all three phthalate isomers in syntrophic association with a methanogen (Qiu et al ., ).…”

Section: Introductionmentioning

confidence: 99%

Microbial degradation of phthalates: biochemistry and environmental implications

Boll

Geiger

Junghare

et al. 2019

Environ Microbiol Rep

133

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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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Section: Introductionmentioning

confidence: 99%

Microbial degradation of phthalates: biochemistry and environmental implications

Boll

Geiger

Junghare

et al. 2019

Environ Microbiol Rep

133

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“…Only very little is known about anaerobic phthalate degradation in strictly anaerobic bacteria. Phthalate degradation coupled to sulphate reduction and methanogenesis was observed in sediment slurries or enrichment cultures (Kleerebezem et al ., ; Liu and Chi, ; Chang et al ., ; Liu et al ., ; Liu et al ., ), and Pelotomaculum species were reported to degrade phthalate in syntrophic association with hydrogenotrophic methanogens (Qiu et al ., ). However, the genes and enzymes involved in phthalate degradation have not yet been studied in an obligately anaerobic organism.…”

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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“…ATBC28, there was no clear differentiation between the short- and long-chain pathways when growing with either DBP or DEHP (Figure ). DBP is possibly catabolized via benzoate, as shown in Figure 2 and previously suggested. − Benzoate could then be processed via three different pathways (Figure ): (1) it is converted to maleate and pyruvate via 3-hydroxy benzoate, gentisate, and 3-maleyl pyruvate, although no enzyme has been described in KEGG for the conversion of benzoate to 3-hydroxy benzoate, (2) it follows the same pathway for protocatechuate degradation as seen in Mycobacterium sp. DBP42, via an initial conversion of the benzoate to either 3- (as above) or 4-hydroxy benzoate (by a cytochrome P450 monooxygenase; not detected in the genome), and then protocatechuate, or (3) it is converted to cis -1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate and then catechol by benzoate 1,2-dioxygenases and dihydroxycyclohexadiene carboxylate dehydrogenase after which it is funneled back into the β-ketoadipate pathway via cis , cis -muconate and muconolactone.…”

Section: Resultsmentioning

confidence: 82%

Plasticizer Degradation by Marine Bacterial Isolates: A Proteogenomic and Metabolomic Characterization

Wright

Bosch

Gibson

et al. 2020

Environ. Sci. Technol.

133

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Many commercial plasticizers are toxic endocrine-disrupting chemicals that are added to plastics during manufacturing and may leach out once they reach the environment. Traditional phthalic acid ester plasticizers (PAEs), such as dibutyl phthalate (DBP) and bis(2-ethyl hexyl) phthalate (DEHP), are now increasingly being replaced with more environmentally friendly alternatives, such as acetyl tributyl citrate (ATBC). While the metabolic pathways for PAE degradation have been established in the terrestrial environment, to our knowledge, the mechanisms for ATBC biodegradation have not been identified previously and plasticizer degradation in the marine environment remains underexplored. From marine plastic debris, we enriched and isolated microbes able to grow using a range of plasticizers and, for the first time, identified the pathways used by two phylogenetically distinct bacteria to degrade three different plasticizers (i.e., DBP, DEHP, and ATBC) via a comprehensive proteogenomic and metabolomic approach. This integrated multi-OMIC study also revealed the different mechanisms used for ester side-chain removal from the different plasticizers (esterases and enzymes involved in the β-oxidation pathway) as well as the molecular response to deal with toxic intermediates, that is, phthalate, and the lower biodegrading potential detected for ATBC than for PAE plasticizers. This study highlights the metabolic potential that exists in the biofilms that colonize plasticsthe Plastisphereto effectively biodegrade plastic additives and flags the inherent importance of microbes in reducing plastic toxicity in the environment.

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CO2–H2-dependent anaerobic biotransformation of phthalic acid isomers in sediment slurries

Cited by 25 publications

References 28 publications

Microbial degradation of phthalates: biochemistry and environmental implications

Microbial degradation of phthalates: biochemistry and environmental implications

Enzymes involved in phthalate degradation in sulphate‐reducing bacteria

Plasticizer Degradation by Marine Bacterial Isolates: A Proteogenomic and Metabolomic Characterization

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