The aerobic metabolism of cyclohexanecarboxylic acid by <i>Acinetobacter anitratum</i>

Rho, Elmer; Evans, William C.

doi:10.1042/bj1480011

Cited by 43 publications

(18 citation statements)

References 16 publications

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“…Similarly, Corynebacterium cyclohexanicum (Tokuyama and Kaneda, 1973) and Acinetobacter spp. (Rho and Evans, 1975;Herman et al, 1993) have also been shown to degrade cyclohexanecarboxylic acid and carboxylated cycloalkanes. In our study, no sequences relating to Corynebacterium spp.…”

Section: Discussionmentioning

confidence: 99%

“…Several microorganisms including: Acinetobacter anitratum, Alcaligenes faecalis and Pseudomonas putida have been shown to metabolize model NAs by aerobic b-oxidation pathways (Blakley, 1974;Rho and Evans, 1975;Blakley and Papish, 1982). Alcaligenes sp.…”

Section: Discussionmentioning

confidence: 99%

“…Despite their persistence and toxicity, very little is known about NA biodegradation. Studies using model compounds (chemically synthesized in the laboratory) and commercial compounds (derived during petroleum fractionation) have provided an insight into the NA metabolic pathways (Rho and Evans, 1975;Taylor and Trudgill, 1978;Clemente et al, 2004;Smith et al, 2008). On the basis of these findings, biodegradation is affected by chemical structure (Whitby, 2010): generally, the more recalcitrant NAs have high molecular weights, contain multiple branched alkyl chains and methyl substituted cycloalkane rings Paslawski et al, 2009;Videla et al, 2009).…”

Section: Introductionmentioning

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: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

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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“…Products of biodegradation are often carbon dioxide and new biomass [59], but complete mineralization would yield only carbon dioxide and water. A number of microorganisms have the ability to metabolize NAs, including Acinetobacter anitratum, Alcaligenes faecalis, and Pseudomonas putida [60][61][62][63]. It is believed that the degradation pathway is dominated by b-oxidation, but a-oxidation and aromatization may also play a contributing role [64].…”

Section: Biodegradationmentioning

confidence: 99%

Water treatment technologies for the remediation of naphthenic acids in oil sands process-affected water

Quinlan

Tam

2015

Chemical Engineering Journal

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“…In the present paper, we report a novel degradation pathway for cyclopropanecarboxylate in R. rhodochrous. It has been reported that cyclohexanecarboxylate and cyclopentanecarboxylate are metabolized by bacteria through a pathway involving ␤-oxidation of coenzyme A (CoA) intermediates (4,22).…”

mentioning

confidence: 99%

Novel Pathway for Utilization of Cyclopropanecarboxylate by Rhodococcus rhodochrous

Toraya

Oka

Ando

et al. 2004

Appl Environ Microbiol

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A new strain isolated from soil utilizes cyclopropanecarboxylate as the sole source of carbon and energy and was identified as Rhodococcus rhodochrous (H. Nishihara, Y. Ochi, H. Nakano, M. Ando, and T. Toraya, J. Ferment. Bioeng. 80:400-402, 1995). A novel pathway for the utilization of cyclopropanecarboxylate, a highly strained compound, by this bacterium was investigated. Cyclopropanecarboxylate-dependent reduction of NAD ؉ in cell extracts of cyclopropanecarboxylate-grown cells was observed. When intermediates accumulated in vitro in the absence of NAD ؉ were trapped as hydroxamic acids by reaction with hydroxylamine, cyclopropanecarboxohydroxamic acid and 3-hydroxybutyrohydroxamic acid were formed. Cyclopropanecarboxyl-coenzyme A (CoA), 3-hydroxybutyryl-CoA, and crotonyl-CoA were oxidized with NAD ؉ in cell extracts, whereas methacrylyl-CoA and 3-hydroxyisobutyryl-CoA were not. When both CoA and ATP were added, organic acids corresponding to the former three CoA thioesters were also oxidized in vitro by NAD ؉ , while methacrylate, 3-hydroxyisobutyrate, and 2-hydroxybutyrate were not. Therefore, it was concluded that cyclopropanecarboxylate undergoes oxidative degradation through cyclopropanecarboxyl-CoA and 3-hydroxybutyryl-CoA. The enzymes catalyzing formation and ring opening of cyclopropanecarboxyl-CoA were shown to be inducible, while other enzymes involved in the degradation were constitutive.

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The aerobic metabolism of cyclohexanecarboxylic acid by Acinetobacter anitratum

Cited by 43 publications

References 16 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

Water treatment technologies for the remediation of naphthenic acids in oil sands process-affected water

Novel Pathway for Utilization of Cyclopropanecarboxylate by Rhodococcus rhodochrous

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