Identification of alkaline phosphatase genes for utilizing a flame retardant, tris(2-chloroethyl) phosphate, in Sphingobium sp. strain TCM1

Takahashi, Shouji; Hiroshi, Katanuma; Abe, Katsumasa; Kera, Yoshio

doi:10.1007/s00253-016-7991-9

Cited by 33 publications

(22 citation statements)

References 28 publications

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“…It is considered that a phosphotriesterase, PDE and PME are involved in the degradation of TCEP. While phosphoesterases catalyzing the first and third steps of TCEP degradation in TCM1 have been identified in our previous studies as a HAD 9 and an alkaline phosphatase 10 respectively, no information has been reported on a PDE from this microorganism. In the present study, Sb -PDE from Sphingobium sp.…”

Section: Discussionmentioning

confidence: 83%

“…However, it has already been reported that two alkaline phosphatases, SbPhoA and SbPhoX-II, are involved in the utilization of TCEP by Sphingobium sp. strain TCM1 and the double gene mutant did not grow on TCEP medium 10 . These results suggest that Sb -PDE catalyzes only the second step in the degradation of organophosphorus triesters, and not the third (phosphomonoester hydrolysis) step, although the PME activity of the enzyme toward monohaloalkyl phosphate was not determined in this study.…”

Section: Discussionmentioning

confidence: 99%

“…Subsequently, a phosphotriesterase catalyzing the first step of TCEP and TDCPP degradation, named haloalkylphosphorus hydrolase (HAD), was cloned and purified 8, 9 . We also recently reported that two alkaline phosphatases, which are metal-dependent phosphomonoesterases (PMEs) named SbPhoA and SbPhoX-II, are involved in the metabolism of TCEP 10 . However, no information has been reported on a phosphodiesterase (PDE) catalyzing the second step of TCEP degradation.…”

Section: Introductionmentioning

confidence: 99%

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An atypical phosphodiesterase capable of degrading haloalkyl phosphate diesters from Sphingobium sp. strain TCM1

Abe

Mukai

Morooka

et al. 2017

Sci Rep

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Sphingobium sp. strain TCM1 can degrade tris(2-chloroethyl) phosphate (TCEP) to inorganic phosphate and 2-chloroethanol. A phosphotriesterase (PTE), phosphodiesterase (PDE) and phosphomonoesterase (PME) are believed to be involved in the degradation of TCEP. The PTE and PME that respectively catalyze the first and third steps of TCEP degradation in TCM1 have been identified. However, no information has been reported on a PDE catalyzing the second step. In this study, we identified, purified, and characterized a PDE capable of hydrolyzing haloalkyl phosphate diesters. The final preparation of the enzyme had a specific activity of 29 µmol min−1 mg−1 with bis(p-nitrophenyl) phosphate (BpNPP) as the substrate. It also possessed low PME activity with p-nitrophenyl phosphate (pNPP) as substrate. The catalytic efficiency (k cat/K m) with BpNPP was significantly higher than that with pNPP, indicating that the enzyme prefers the organophosphorus diester to the monoester. The enzyme degraded bis(2,3-dibromopropyl) phosphate, bis(1,3-dichloro-2-propyl) phosphate and bis(2-chloroethyl) phosphate, suggesting that it is involved in the metabolism of haloalkyl organophosphorus triesters. The primary structure of the PDE from TCM1 is distinct from those of typical PDE family members and the enzyme belongs to the polymerase and histidinol phosphatase superfamily.

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Section: Discussionmentioning

confidence: 83%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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An atypical phosphodiesterase capable of degrading haloalkyl phosphate diesters from Sphingobium sp. strain TCM1

Abe

Mukai

Morooka

et al. 2017

Sci Rep

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“…The OPs used in our MIX treatment are proven to be degradable and hence can be used as a resource for bacteria (Leahy and Colwell, ; Takahashi et al ., , , , ; Seo et al ., ; Abe et al ., , ; Joye et al ., ; Kera et al ., ; Vila‐Costa et al ., )). Yet, our study showed notably negative effects on bacterial growth of hydrocarbons and OPEs supplied at environmentally relevant concentrations.…”

Section: Discussionmentioning

confidence: 99%

Direct effects of organic pollutants on the growth and gene expression of the Baltic Sea model bacteriumRheinheimerasp.BAL341

Karlsson

Cerro‐Gálvez

Lundin

et al. 2019

Microbial Biotechnology

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Summary Organic pollutants (OPs) are critically toxic, bioaccumulative and globally widespread. Moreover, several OPs negatively influence aquatic wildlife. Although bacteria are major drivers of the ocean carbon cycle and the turnover of vital elements, there is limited knowledge of OP effects on heterotrophic bacterioplankton. We therefore investigated growth and gene expression responses of the Baltic Sea model bacterium Rheinheimera sp. BAL341 to environmentally relevant concentrations of distinct classes of OPs in 2‐h incubation experiments. During exponential growth, exposure to a mix of polycyclic aromatic hydrocarbons, alkanes and organophosphate esters (denoted MIX) resulted in a significant decrease (between 9% and 18%) in bacterial abundance and production compared with controls. In contrast, combined exposure to perfluorooctanesulfonic acids and perfluorooctanoic acids (denoted PFAS) had no significant effect on growth. Nevertheless, MIX and PFAS exposures both induced significant shifts in gene expression profiles compared with controls in exponential growth. This involved several functional metabolism categories (e.g. stress response and fatty acids metabolism), some of which were pollutant‐specific (e.g. phosphate acquisition and alkane‐1 monooxygenase genes). In stationary phase, only two genes in the MIX treatment were significantly differentially expressed. The substantial direct influence of OPs on metabolism during bacterial growth suggests that widespread OPs could severely alter biogeochemical processes governed by bacterioplankton.

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“…strain TCM1. The successive cleavage of the phosphate ester bond is a common step in the biodegradation of OPFRs such as TCEP, TBP and TPP [15,29,36]. The biodegradation path of TCPP and its derivative molecule TCPP-OH was simulated in accordance with the biodegradation path of TBP, which led to the greatest improvement in biodegradation and photodegradation and deduction of microbial degradation products (Figure 3).…”

Section: Mechanistic Analysis For the Enhancement Of Biodegradation Fmentioning

confidence: 99%

Enhanced Biodegradation/Photodegradation of Organophosphorus Fire Retardant Using an Integrated Method of Modified Pharmacophore Model with Molecular Dynamics and Polarizable Continuum Model

Yang

Liu

2020

Polymers

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A comprehensive 3D-quantitative structure–activity relationship (QSAR) pharmacophore model was constructed using the values of comprehensive biodegradation/photodegradation effects of 17 organophosphorus flame retardants (OPFRs) evaluated by a normalization method to modify OPFRs with high biodegradation/photodegradation, taking tris(chloro-isopropyl) phosphate (TCPP), tris(2-chloroethyl) phosphate (TCEP) and tris(1-chloro-2-propyl) phosphate (TCIPP)—which occur frequently in the environment, and are the most difficult to degrade as target molecules. OPFR-derivative molecules TCPP–OH shows the highest improvement in biodegradation and photodegradation (55.48% and 46.37%, respectively). On simulating the biodegradation path and photodegradation path, it is found that the energy barrier of TCPP–OH for phosphate bond cleavage is reduced by 15.73% and 52.52% compared to TCPP after modification, respectively. Finally, in order to further significantly improve its biodegradability and photodegradation, the efficiency enhancement in the biodegradation and photodegradation of TCPP–OH are analyzed under the simulated environment by molecular dynamics and polarizable continuum model, respectively. The results of molecular dynamics show that the biodegradation efficiency of the TCPP–OH increased by 75.52% compared to TCPP. The UV spectral transition energy (4.07 eV) of TCPP–OH under the influence of hydrogen peroxide solvation effect is 44.23% lower than the actual transition energy (7.29 eV) of TCPP.

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Identification of alkaline phosphatase genes for utilizing a flame retardant, tris(2-chloroethyl) phosphate, in Sphingobium sp. strain TCM1

Cited by 33 publications

References 28 publications

An atypical phosphodiesterase capable of degrading haloalkyl phosphate diesters from Sphingobium sp. strain TCM1

An atypical phosphodiesterase capable of degrading haloalkyl phosphate diesters from Sphingobium sp. strain TCM1

Direct effects of organic pollutants on the growth and gene expression of the Baltic Sea model bacteriumRheinheimerasp.BAL341

Enhanced Biodegradation/Photodegradation of Organophosphorus Fire Retardant Using an Integrated Method of Modified Pharmacophore Model with Molecular Dynamics and Polarizable Continuum Model

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