The microbial degradation of cyclohexanecarboxylic acid by a β-oxidation pathway with simultaneous induction to the utilization of benzoate

Blakley, E. R.

doi:10.1139/m78-141

Cited by 55 publications

(28 citation statements)

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“…To date, there are no reports of any of these microorganisms being involved in NAdegradation. Achromobacter spp., which have been shown to degrade cyclohexanecarboxylic acid and carboxylated cycloalkane by others (Blakley, 1974(Blakley, , 1978, were in low abundance in our study. Similarly, Corynebacterium cyclohexanicum (Tokuyama and Kaneda, 1973) and Acinetobacter spp.…”

Section: Discussioncontrasting

confidence: 47%

“…However, pathways have been proposed for the biodegradation of aliphatic and alicyclic carboxylic acids and include b-oxidation (Blakley, 1978;Blakley and Papish, 1982;Alexander, 1999;Quagraine et al, 2005a), combined a-and b-oxidation (Beam and Perry, 1974;Rontani and Bonin, 1992) and aromatization (Blakley, 1974;Taylor and Trudgill, 1978;Trudgill, 1984). In this work, we sought to elucidate the initial steps involved in aromatic alkanoic acid metabolism.…”

Section: Discussionmentioning

confidence: 99%

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Microbial biodegradation of aromatic alkanoic naphthenic acids is affected by the degree of alkyl side chain branching

Johnson

Smith²,

Sutton

et al. 2010

The ISME Journal

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Naphthenic acids (NAs) occur naturally in oil sands and enter the environment through natural and anthropogenic processes. NAs comprise toxic carboxylic acids that are difficult to degrade. Information on NA biodegradation mechanisms is limited, and there are no studies on alkyl branched aromatic alkanoic acid biodegradation, despite their contribution to NA toxicity and recalcitrance. Increased alkyl side chain branching has been proposed to explain NA recalcitrance. Using soil enrichments, we examined the biodegradation of four aromatic alkanoic acid isomers that differed in alkyl side chain branching: (4 0 -n-butylphenyl)-4-butanoic acid (n-BPBA, least branched); (4 0 -iso-butylphenyl)-4-butanoic acid (iso-BPBA); (4 0 -sec-butylphenyl)-4-butanoic acid (sec-BPBA) and (4 0 -tert-butylphenyl)-4-butanoic acid (tert-BPBA, most branched). n-BPBA was completely metabolized within 49 days. Mass spectral analysis confirmed that the more branched isomers iso-, sec-and tert-BPBA were transformed to their butylphenylethanoic acid (BPEA) counterparts at 14 days. The BPEA metabolites were generally less toxic than BPBAs as determined by Microtox assay. n-BPEA was further transformed to a diacid, showing that carboxylation of the alkyl side chain occurred. In each case, biodegradation of the carboxyl side chain proceeded through betaoxidation, which depended on the degree of alkyl side chain branching, and a BPBA degradation pathway is proposed. Comparison of 16S rRNA gene sequences at days 0 and 49 showed an increase and high abundance at day 49 of Pseudomonas (sec-BPBA), Burkholderia (n-, iso-, tert-BPBA) and Sphingomonas (n-, sec-BPBA).

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Section: Discussioncontrasting

confidence: 47%

Section: Discussionmentioning

confidence: 99%

Microbial biodegradation of aromatic alkanoic naphthenic acids is affected by the degree of alkyl side chain branching

Johnson

Smith²,

Sutton

et al. 2010

The ISME Journal

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“…A glutaryl-CoA dehydrogenase was significantly produced in crude extracts of bacteria growing anaerobically in aromatic compounds (and cyclohexane carboxylate), which suggests that glutaryl-CoA was indeed an intermediate formed during the catabolism of these compounds via the pimelyl-CoA/3-hydroxypimelyl-CoA ␤-oxidation pathway (28,106,118,140,141,153,328). Recently, the gcdH gene, encoding the bifunctional glutaryl-CoA dehydrogenase enzyme, has been identified and characterized for Azoarcus sp.…”

Section: Benzoate Catabolism: the Benzoyl-coa Degradation Pathwaymentioning

confidence: 99%

Anaerobic Catabolism of Aromatic Compounds: a Genetic and Genomic View

Carmona

Zamarro

Blázquez

et al. 2009

Microbiol Mol Biol Rev

388

381

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SUMMARY Aromatic compounds belong to one of the most widely distributed classes of organic compounds in nature, and a significant number of xenobiotics belong to this family of compounds. Since many habitats containing large amounts of aromatic compounds are often anoxic, the anaerobic catabolism of aromatic compounds by microorganisms becomes crucial in biogeochemical cycles and in the sustainable development of the biosphere. The mineralization of aromatic compounds by facultative or obligate anaerobic bacteria can be coupled to anaerobic respiration with a variety of electron acceptors as well as to fermentation and anoxygenic photosynthesis. Since the redox potential of the electron-accepting system dictates the degradative strategy, there is wide biochemical diversity among anaerobic aromatic degraders. However, the genetic determinants of all these processes and the mechanisms involved in their regulation are much less studied. This review focuses on the recent findings that standard molecular biology approaches together with new high-throughput technologies (e.g., genome sequencing, transcriptomics, proteomics, and metagenomics) have provided regarding the genetics, regulation, ecophysiology, and evolution of anaerobic aromatic degradation pathways. These studies revealed that the anaerobic catabolism of aromatic compounds is more diverse and widespread than previously thought, and the complex metabolic and stress programs associated with the use of aromatic compounds under anaerobic conditions are starting to be unraveled. Anaerobic biotransformation processes based on unprecedented enzymes and pathways with novel metabolic capabilities, as well as the design of novel regulatory circuits and catabolic networks of great biotechnological potential in synthetic biology, are now feasible to approach.

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“…Recently, it has been shown for methanogenic enrichment cultures that longchain dicarboxylic acids of chain lengths C6-Clo are Poxidized rather than decarboxylated (Matthies & Schink, 1993). In such a pathway of pimelate degradation, 3-oxopimelyl-CoA would be produced before thiolytic cleavage to glutaryl-CoA and acetyl-CoA occurs (Blakley, 1978). Further degradation of glutaryl-CoA, which also cannot be directly decarboxylated for the same reasons as mentioned above, has been elucidated for another Pseudomonas-like bacterium (Numa et al, 1964).…”

Section: Discussionmentioning

confidence: 97%

“…Presumably, the acid is first activated, yielding pimelyl-mono-Co A. Pimelyl-Coh is expected to be degraded via glutaryl-CoA to three acetyl-CoA residues plus one CO, (Blakley, 1978). In the present study, the anaerobic degradation of pimelate was investigated taking into account that this pathway might be linked to that of anaerobic benzoate degradation by a common intermediate.…”

Section: Introductionmentioning

confidence: 99%

Anaerobic degradation of pimelate by newly isolated denitrifying bacteria

Gallus

Schink

1994

Microbiology

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A C, dicarboxylic (pimelic) acid derivative is postulated as an intermediate in anaerobic degradation of benzoate. Four strains of Gram-negative, nitratereducing bacteria capable of growth with both pimelate and benzoate as sole carbon and energy source were isolated. The metabolism of strain LP-1, which was enriched from activated sludge with pimelate as substrate, was studied in detail. This strain grew only with oxygen or with oxidized nitrogen compounds as electron acceptor. In the presence of nitrate, a wide range of substrates excluding C, compounds was degraded. The new isolate was catalase-and oxidase-positive, and had one single polar f lagellum. Strain LP-1 was tentatively classified within the family Pseudomonadaceae. The catabolism of pimelate and benzoate was studied in cell-free extracts of strain LP-1. Both acids were activated with coenzyme A in a Mg2+-and ATP-dependent reaction. The corresponding acyl-CoA synthetases were specifically induced by the respective growth substrate. Pimelate was also activated by CoA transfer from succinyl-CoA. Pimelyl-CoA was oxidized by cell-free extracts in the presence of potassium ferricyanide. Degradation to glutaryl-CoA and acetyl-CoA proceeded by a sequence of P-oxidation-like reactions. Glutaryl-CoA dehydrogenase and glutaconyl-CoA decarboxylase activities were expressed in cells grown with pimelate or benzoate, indicating the specific involvement of these enzyme activities in anaerobic degradation of these two acids. Enzyme activities responsible for further degradation of the resulting crotonyl-CoA to acetylCoA via classical /?-oxidation were also detected.

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The microbial degradation of cyclohexanecarboxylic acid by a β-oxidation pathway with simultaneous induction to the utilization of benzoate

Cited by 55 publications

References 0 publications

Microbial biodegradation of aromatic alkanoic naphthenic acids is affected by the degree of alkyl side chain branching

Microbial biodegradation of aromatic alkanoic naphthenic acids is affected by the degree of alkyl side chain branching

Anaerobic Catabolism of Aromatic Compounds: a Genetic and Genomic View

Anaerobic degradation of pimelate by newly isolated denitrifying bacteria

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