Anaerobic Mineralization of Stable-Isotope-Labeled 2-Methylnaphthalene

Sullivan, Elise R.; Zhang, Xiaoming; Phelps, Craig D.; Young, L. Y.

doi:10.1128/aem.67.9.4353-4357.2001

Cited by 47 publications

(62 citation statements)

References 17 publications

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“…In cases where PAHs were activated by other mechanisms and subsequently metabolized, no label was found in carboxylated metabolites after incubation with 13 C-bicarbonate. For instance, 2-methylnapthalene-degrading enrichments produced 2-naphthoic acid, but did not incorporate 13 C in the carboxyl group of the metabolite when incubated with labeled bicarbonate (Sullivan et al, 2001). Similarly, a sulfidogenic consortium capable of benzene mineralization did not incorporate 13 Ccarbon in the carboxyl group of benzoate when the cells were supplemented with 13 C-bicarbonate, suggesting that the carboxyl group in the metabolite was not a product of direct carboxylation .…”

Section: Discussionmentioning

confidence: 99%

“…To our knowledge, this is the first determination of the 16S rRNA sequence phylogeny of a sulfate-reducing phenanthrene-degrading culture. To date, two possible mechanisms for anaerobic PAH activation have been reported, with most work focused on the metabolism of two-ring compounds such as naphthalene and 2-methylnaphthalene (Sullivan et al, 2001;Annweiler et al, 2000Annweiler et al, , 2002. Only one study has helped clarify the metabolism of phenanthrene (Zhang and Young, 1997).…”

Section: Discussionmentioning

confidence: 99%

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Anaerobic phenanthrene mineralization by a carboxylating sulfate-reducing bacterial enrichment

et al. 2007

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Information on the susceptibility of higher molecular weight polynuclear aromatic hydrocarbons to anaerobic biodegradation is relatively rare. We obtained a sulfate-reducing bacterial enrichment capable of phenanthrene metabolism from a hydrocarbon-contaminated marine sediment. Phenanthrene degradation was in stoichiometric agreement with the theoretically expected amount of sulfate reduction and inhibited by molybdate. Mineralization of 14 C-phenanthrene by the enrichment was confirmed by the recovery of the expected amount of 14 CO 2 . Stable isotope studies with protonated or deuterated phenanthrene resulted in the detection of the correspondingly labeled phenanthrene carboxylic acid by gas chromatography-mass spectrometry. Comparison of the metabolite profile with a synthesized standard confirmed that the parent molecule was carboxylated at the C-2 position. Incorporation of 13 C-bicarbonate into the carboxyl group implicated a direct carboxylation of phenanthrene as a likely key initial reaction. Denaturing gradient gel electrophoresis analysis of the enrichment showed only two major bands and 16S rRNA sequences obtained by cloning clustered with known hydrocarbon-degrading sulfate-reducing d-proteobacteria, indicating their possible involvement in the anaerobic oxidation of phenanthrene via carboxylation as the initial activation reaction.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Anaerobic phenanthrene mineralization by a carboxylating sulfate-reducing bacterial enrichment

et al. 2007

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“…3 c). A pathway producing carboxylated 2-methylnaphthalene has been suggested [Sullivan et al, 2001] but not fully deduced (not shown). However, analogous to the differential susceptibility of xylene isomers, considerably more experimentation will be required to elucidate the biodegradability of 1-methylnaphthalene and its potential metabolites, as its degradation is not simply analogous to the more susceptible isomer 2-methylnaphthalene.…”

Section: Alkyl-pahs: 2-methylnaphthalene and 1-methylnaphthalenementioning

confidence: 99%

Anaerobic Biodegradation of Aromatic Hydrocarbons: Pathways and Prospects

Foght¹

2008

Microb Physiol

271

151

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Aromatic hydrocarbons contaminate many environments worldwide, and their removal often relies on microbial bioremediation. Whereas aerobic biodegradation has been well studied for decades, anaerobic hydrocarbon biodegradation is a nascent field undergoing rapid shifts in concept and scope. This review presents known metabolic pathways used by microbes to degrade aromatic hydrocarbons using various terminal electron acceptors; an outline of the few catabolic genes and enzymes currently characterized; and speculation about current and potential applications for anaerobic degradation of aromatic hydrocarbons.

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“…They proved to be useful tools for examining the initial mechanisms of attack on compounds such as benzene, naphthalene, and phenanthrene and alkane degradation by strain AK-01 (30,38,39,48,49). In this report, we present the results of an investigation of the initial reactions of alkane degradation by strain Hxd3.…”

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confidence: 99%

Anaerobic Transformation of Alkanes to Fatty Acids by a Sulfate-Reducing Bacterium, Strain Hxd3

Phelps

Young

2003

Appl Environ Microbiol

Self Cite

162

106

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Strain Hxd3, an alkane-degrading sulfate reducer previously isolated and described by Aeckersberg et al. (F. Aeckersberg, F. Bak, and F. Widdel, Arch. Microbiol. 156:5-14, 1991), was studied for its alkane degradation mechanism by using deuterium and 13 C-labeled compounds. Deuterated fatty acids with even numbers of C atoms (C-even) and 13 C-labeled fatty acids with odd numbers of C atoms (C-odd) were recovered from cultures of Hxd3 grown on perdeuterated pentadecane and [1,2-13 C 2 ]hexadecane, respectively, underscoring evidence that C-odd alkanes are transformed to C-even fatty acids and vice versa. When Hxd3 was grown on unlabeled hexadecane in the presence of [ 13 C]bicarbonate, the resulting 15:0 fatty acid, which was one carbon shorter than the alkane, incorporated a 13 C label to form its carboxyl group. The same results were observed when tetradecane, pentadecane, and perdeuterated pentadecane were used as the substrates. These observations indicate that the initial attack of alkanes includes both carboxylation with inorganic bicarbonate and the removal of two carbon atoms from the alkane chain terminus, resulting in a fatty acid one carbon shorter than the original alkane. The removal of two terminal carbon atoms is further evidenced by the observation that the [1,2-13 C 2 ]hexadecane-derived fatty acids contained either two 13 C labels located exclusively at their acyl chain termini or none at all. Furthermore, when perdeuterated pentadecane was used as the substrate, the 14:0 and 16:0 fatty acids formed both carried the same numbers of deuterium labels, while the latter was not deuterated at its carboxyl end. These observations provide further evidence that the 14:0 fatty acid was initially formed from perdeuterated pentadecane, while the 16:0 fatty acid was produced after chain elongation of the former fatty acid with nondeuterated carbon atoms. We propose that strain Hxd3 anaerobically transforms an alkane to a fatty acid through a mechanism which includes subterminal carboxylation at the C-3 position of the alkane and elimination of the two adjacent terminal carbon atoms.

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Anaerobic Mineralization of Stable-Isotope-Labeled 2-Methylnaphthalene

Cited by 47 publications

References 17 publications

Anaerobic phenanthrene mineralization by a carboxylating sulfate-reducing bacterial enrichment

Anaerobic phenanthrene mineralization by a carboxylating sulfate-reducing bacterial enrichment

Anaerobic Biodegradation of Aromatic Hydrocarbons: Pathways and Prospects

Anaerobic Transformation of Alkanes to Fatty Acids by a Sulfate-Reducing Bacterium, Strain Hxd3

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