Bacterial scission of ether bonds.

White, Graham F.; Russell, Nicholas J.; Tidswell, Edward C.

doi:10.1128/mmbr.60.1.216-232.1996

Cited by 128 publications

(52 citation statements)

References 94 publications

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“…Thus, the ether bond must be the reason for the incomplete breakdown of DEGDB. This particular chemical bond has been found to be resistant to biodegradation [27], and its presence adds to the stability of the monoester. Any mechanism of biodegradation of any of these dibenzoates would be expected to start with the loss of one benzoate group due to hydrolysis.…”

Section: Biodegradation Of Pddbmentioning

confidence: 99%

Characterization of 1,5‐pentanediol dibenzoate as a potential “green” plasticizer for poly(vinyl chloride)

Firlotte

Cooper

Marić

et al. 2009

Vinyl Additive Technology

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1,5-Pentanediol dibenzoate (PDDB) was evaluated as a potential ''green'' plasticizer for poly(vinyl chloride) (PVC) at concentrations ranging between 20 and 80 parts by weight per hundred parts of resin. The results of glass transition temperature (T g ) and tensile tests of PDDB blends with PVC were compared with those for blends of the commercial plasticizers di(2-ethylhexyl) phthalate (DEHP), di(ethylene glycol) dibenzoate (DEGDB), and di(propylene glycol) dibenzoate (DPGDB) in PVC. The depression in T g and the tensile properties were comparable for a PDDB/PVC blend at a fixed composition to those of blends with DEHP, DEGDB, and DPGDB. The PDDB was subjected to biodegradation using co-metabolism by the common soil bacterium Rhodococcus rhodochrous (ATCC 13808). After 16 days of growth, nearly all of the PDDB was degraded, and only small amounts of transient, unidentified metabolites were observed in the growth medium during the experiment. J. VINYL ADDIT. TECHNOL., 15:99-107, 2009. ª

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Section: Biodegradation Of Pddbmentioning

confidence: 99%

Characterization of 1,5‐pentanediol dibenzoate as a potential “green” plasticizer for poly(vinyl chloride)

Firlotte

Cooper

Marić

et al. 2009

Vinyl Additive Technology

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“…The 0-demethylation of phenyl-methyl ethers has been demonstrated in acetogenic bacteria of the genera Acetobucterium (Bache and Pfennig, 1981), Clostridiurn, Sporomusa and relatives (DeWeerd et al, 1988). These bacteria only utilize the methyl group of the substrate for growth and excrete the demethylated aromatic scaffold into the medium (reviewed by Stupperich, 1993;White et al, 1996). O-demethylation of 3,4-dimethoxybenzoate and other methoxy-substituted aromatic compounds has been demonstrated in cell-free extracts of S. ovata and A. woodii (Berman and Frazer, 1992;Stupperich and Konle, 1993;Stupperich et al, 1996).…”

Section: -Demethylationmentioning

confidence: 99%

“…The latter are the focus of this review. Several good reviews are available on other aspects of this theme (Dagley, 1971;Evans, 1977;Kaiser and Hanselmann, 1982;Sleat and Robinson, 1984;Young, 1984;Berry et al, 1987;Hopper, 1987;Evans and Fuchs, 1988;Hegemann, 1988;Schink and Tschech, 1988;Mohn and Tiedje, 1992;Schink et al, 1992;Stupperich, 1993;Elder and Kelly, 1994;Fetzner and Lingens, 1994;Fuchs et al, 1994;Gibson and Harwood, 1995a,b;Frazer et al, 1995;Villemur, 1995;White et al, 1996;Holhger and Zehnder, 1996).…”

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confidence: 99%

Anaerobic Metabolism of Aromatic Compounds

Heider

Fuchs

1997

European Journal of Biochemistry

285

214

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Aromatic compounds comprise a wide variety of low-molecular-mass natural compounds (amino acids, quinones, flavonoids, etc.) and biopolymers (lignin, melanin). They are almost exclusively degraded by microorganisms. Aerobic aromatic metabolism is characterised by the extensive use of molecular oxygen. Monoxygenases and dioxygenases are essential for the hydroxylation and cleavage of aromatic ring structures. Accordingly, the characteristic central intermediates of the aerobic pathways (e.g. catechol) are readily attacked oxidatively. Anaerobic aromatic catabolism requires, of necessity, a quite different strategy. The basic features of this metabolism have emerged from studies on bacteria that degrade soluble aromatic substrates to CO, in the complete absence of molecular oxygen.Essential to anaerobic aromatic metabolism is the replacement of all the oxygen-dependent steps by an alternative set of novel reactions and the formation of different central intermediates (e.g. benzoylCoA) for breaking the aromaticity and cleaving the ring; notably, in anaerobic pathways, the aromatic ring is reduced rather than oxidised. The two-electron reduction of benzoyl-CoA to a cyclic diene requires the cleavage of two molecules of ATP to ADP and P, and is catalysed by benzoyl-CoA reductase. After nitrogenase, this is the second enzyme known which overcomes the high activation energy required for reduction of a chemically stable bond by coupling electron transfer to the hydrolysis of ATP. The alicyclic product cyclohex-I ,5-diene-l-carboxyl-CoA is oxidised to acetyl-CoA via a modified P-oxidation pathway ; the ring structure is opened hydrolytically. Some phenolic compounds are anaerobically transformed to resorcinol (1,3-dihydroxybenzene) or phloroglucinol (1,3,5-trihydroxybenzene). These intermediates are also first reduced and then as alicyclic products oxidised to acetyl-CoA.This review gives an outline of the anaerobic pathways which allow bacteria to utilize aromatics even in the absence of oxygen. We focus on previously unknown reactions and on the enzymes characteristic for such novel metabolism.Keywords ; aromatic metabolism ; benzoyl-CoA ; anaerobic bacteria ; aromatic-ring reduction ; phloroglucinol; resorcinol.This review deals with the art of degrading aromatic compounds to CO, in the complete absence of molecular oxygen. This ability allows bacteria to make use of natural compounds of this widespread class as substrates for growth under anoxic conditions. In nature, anoxic conditions are created when oxygen consumption exceeds its supply. This situation prevails in many environments, e.g. in the intestinal tract of animals and man, in the sediments of all natural bodies of water, in ground water and in part in soil. Aromatic compounds are produced or transformed by all organisms, plants being the most prolific producers. There are numerous low-molecular-mass aromatic compounds includ-

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“…In this case, the higher resistance to biodegradation exhibited by MTBE and TAME may be a result of steric hindrance of attacking enzymes. In fact, the accessibility of the methoxy carbon of CH 3 O-MTBE or CH 3 O-TAME is more difficult than that of the ethoxy carbon of CH 3 CH 2 O-ETBE due to the proximity of the ether bond [19,20].…”

Section: Discussionmentioning

confidence: 99%

“…The biological removal of ETBE from contaminated soils and aquifers has not been extensively studied. The cleavage of the ether bond seems to be the major barrier to biodegradation since it demands an appreciable investment of energy to affect cleavage [6][7][8][9][10][11][12]20]. It has recently been reported that propane-oxidizing bacteria were able to degrade ETBE and other gasoline oxygenates, including MTBE and tert-amyl methyl ether (TAME), in an aerobic batch culture [10].…”

Section: Introductionmentioning

confidence: 99%

AEROBIC DEGRADATION OF ETHYL-tert-BUTYL ETHER BY A MICROBIAL CONSORTIUM: SELECTION AND EVALUATION OF BIODEGRADATION ABILITY

Kharoune¹,

Kharoune²,

Lebault³

et al. 2002

Environ Toxicol Chem

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A microbial consortium that degrades ethyl-tert-butyl ether (ETBE) as the sole source of carbon and energy under aerobic conditions was selected from a gasoline-polluted soil. This consortium consists of a variety of microorganisms with a predominance of filamentous morphology. Degradation of ETBE was found to be solely related to bacterial activity. After prolonged cultivation followed by successive transfers, the consortium's degradation ability was improved and reached a specific degradation rate of 95 mg/g(protein)/h (about 146 mg/g(dry wt)/h). This exceeds the previously reported rates in the literature for ETBE-degrading microorganisms as pure or mixed cultures. Furthermore, a stoichiometric balance of chemical oxygen demand (COD) removal and oxygen uptake with ETBE removal provides indirect evidence of complete degradation. The consortium's activity was not inhibited by high ETBE concentrations (< or = 1,600 mg/L), and large inoculum sizes (> or = 120 mg(protein)/L) were desirable for a faster and complete degradation of ETBE. The enriched consortium was also able to completely degrade methyl-tert-butyl ether (MTBE), tert-amyl methyl ether (TAME), and tert-butyl alcohol (TBA). both alone and in mixture with ETBE, without any measurable release of major degradation intermediates. In each case, MTBE and TAME exhibited the most significant resistance to degradation while TBA was rapidly degraded.

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Bacterial scission of ether bonds.

Cited by 128 publications

References 94 publications

Characterization of 1,5‐pentanediol dibenzoate as a potential “green” plasticizer for poly(vinyl chloride)

Characterization of 1,5‐pentanediol dibenzoate as a potential “green” plasticizer for poly(vinyl chloride)

Anaerobic Metabolism of Aromatic Compounds

AEROBIC DEGRADATION OF ETHYL-tert-BUTYL ETHER BY A MICROBIAL CONSORTIUM: SELECTION AND EVALUATION OF BIODEGRADATION ABILITY

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