Degradation of substituted benzoic acids by a Micrococcus species

Haribabu, Bodduluri

doi:10.1016/0378-1097(84)90294-5

Cited by 6 publications

(9 citation statements)

References 12 publications

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“…Induction of GDO was demonstrated in extracts from 4HBA-grown cells, along with stoichiometric accumulation of GA from 4HBA in biotransformation experiments. In contrast, most bacteria aerobically metabolize 4HBA by 3-hydroxylation to yield protocatechuate, which serves as the ring cleavage substrate (25,28,34,35,38,39,55,60,62,64). Metabolism of 4HBA by decarboxylation to phenol, followed by ortho hydroxylation to catechol, has also been suggested in Rhodococcus opacus (35).…”

Section: Discussionmentioning

confidence: 99%

Aerobic Metabolism of 4-Hydroxybenzoic Acid in Archaea via an Unusual Pathway Involving an Intramolecular Migration (NIH Shift)

Fairley

Boyd

Sharma

et al. 2002

Appl Environ Microbiol

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A novel haloarchaeal strain, Haloarcula sp. strain D1, grew aerobically on 4-hydroxybenzoic acid (4HBA) as a sole carbon and energy source and is the first member of the domain Archaea reported to do so. Unusually, D1 metabolized 4HBA via gentisic acid rather than via protocatechuic acid, hydroquinone, or catechol. Gentisate was detected in 4HBA-grown cultures, and gentisate 1,2-dioxygenase activity was induced in 4HBA-grown cells. Stoichiometric accumulation of gentisate from 4HBA was demonstrated in 4HBA-grown cell suspensions containing 2,2-dipyridyl (which strongly inhibits gentisate 1,2-dioxygenase). To establish whether initial 1-hydroxylation of 4HBA with concomitant 1,2-carboxyl group migration to yield gentisate occurred, 2,6-dideutero-4HBA was synthesized and used as a substrate. Deuterated gentisate was recovered from cell suspensions and identified as 3-deutero-gentisate, using gas chromatography-mass spectrometry and proton nuclear magnetic resonance spectroscopy. This structural isomer would be expected only if a 1,2-carboxyl group migration had taken place, and it provides compelling evidence that the 4HBA pathway in Haloarcula sp. strain D1 involves a hydroxylation-induced intramolecular migration. To our knowledge, this is the first report of a pathway which involves such a transformation (called an NIH shift) in the domain Archaea.

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Section: Discussionmentioning

confidence: 99%

Aerobic Metabolism of 4-Hydroxybenzoic Acid in Archaea via an Unusual Pathway Involving an Intramolecular Migration (NIH Shift)

Fairley

Boyd

Sharma

et al. 2002

Appl Environ Microbiol

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“…The electron impact mass spectrum of the isolated material had a molecular ion (M+) at mle 244, with a dominant fragment at 213 [(HOC6H5)2C+CH3]. 'H NMR (CD3CN, 500 MHz; reference, tetramethylsilane [TMS]) had the following ppm: 1.57 (s, 3H), 2.62 (t, aliphatic OH, J = 6 Hz), 3.88 (d, 2H, J = 6 Hz), 6.69 (m, 4H), 6.74 (s, 2H, phenolic OH), and 7.03 (m, 4H). 13C NMR (CD30D, 125 MHz; reference, CD30D) had the following ppm: 24.40 (CH3), 46.48 (C2), 69.85 (CH2OH), 114.04 (meta), 128.07 (ortho), 138.39 (ipso), and 154.63 (para).…”

Section: Co2mentioning

confidence: 99%

“…The electron impact mass spectrum of the isolated material had a small M+ at mle 260, with the most abundant ion at mle 242 (loss of H20) and dominant fragments at mle 136 (HOC6 H4C2H30) and mle 107 (HOC6H4CH2+). 'H NMR (CD3 CN, 200 MHz; reference, TMS) had the following ppm: 2.80 (t, 1H, primary OH), 2.93 (s, 2H, benzylic CH2), 3.07 (s, 1H, tertiary OH), 3.60 (d, 2H, primary alcohol CH2,J = 7.2 Hz), 6.70 and 7.14 (m, 2H each, C2 aryl), 6.56 and 6.79 (m, 2H each, C3 aryl), and 6.62 and 6.75 (broad singlets, phenolic OH). The peaks at 2.80, 3.07, 6.62, and 6.75 all disappeared upon the addition of D20 and the doublet at 3.60 collapsed to a singlet.…”

Section: Co2mentioning

confidence: 99%

Biodegradation of bisphenol A and other bisphenols by a gram-negative aerobic bacterium

Lobos

Leib

1992

Appl Environ Microbiol

215

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A novel bacterium designated strain MV1 was isolated from a sludge enrichment taken from the wastewater treatment plant at a plastics manufacturing facility and shown to degrade 2,2-bis(4-hydroxyphenyl)propane (4,4'-isopropylidenediphenol or bisphenol A). Strain MV1 is a gram-negative, aerobic bacillus that grows on bisphenol A as a sole source of carbon and energy. Total carbon analysis for bisphenol A degradation demonstrated that 60%o of the carbon was mineralized to CO2, 20%o was associated with the bacterial cells, and 20%o was converted to soluble organic compounds. Metabolic intermediates detected in the culture medium during growth on bisphenol A were identified as 4-hydroxybenzoic acid, 4-hydroxyacetophenone, 2,2-bis(4hydroxyphenyl)-1-propanol, and 2,3-bis(4-hydroxyphenyl)-1,2-propanediol. Most of the bisphenol A degraded by strain MV1 is cleaved in some way to form 4-hydroxybenzoic acid and 4-hydroxyacetophenone, which are subsequently mineralized or assimilated into cell carbon. In addition, about 20%o of the bisphenol A is hydroxylated to form 2,2-bis(4-hydroxyphenyl)-1-propanol, which is slowly biotransformed to 2,3-bis(4hydroxyphenyl)-1,2-propanediol. Cells that were grown on bisphenol A degraded a variety of bisphenol alkanes, hydroxylated benzoic acids, and hydroxylated acetophenones during resting-cell assays. Transmission electron microscopy of cells grown on bisphenol A revealed lipid storage granules and intracytoplasmic membranes.

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“…Generally phthalate isomers are degraded via introduction of two hydroxyl groups either at 3,4 or 4,5 position by the aerobic organisms [6][7][8]. The metabolism of homophthalate by the isolated strain follows a different pathway.…”

Section: Discussionmentioning

confidence: 99%

“…degraded o-phthalic acid through the formation of 4,5-dihydroxyphthalate and pro- tocatechuate [6]. Isophthalic acid was degraded through the formation of protocatechuate by a soil bacterium [7]. Terephthalic acid was metabolised through the formation of protocatechuic acid by a Bacillus sp.…”

Section: Introductionmentioning

confidence: 99%

Metabolic pathway of homophthalic acid in Pseudomonas alcaligenes

Karigar

1993

FEMS Microbiology Letters

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A microorganism capable of degrading homophthalic acid as a sole carbon source was isolated from garden soil. The strain was identified as Pseudomonas alcaligenes. The organism degraded homophthalate by a pathway which involved phenylacetate and p-hydroxyphenylacetate as intermediates. The intermediates have been identified by physico-chemical methods. A tentative pathway for the degradation of homophthalate is proposed based on isolation of intermediates, oxygen uptake studies and presence of enzymes involved in the degradation.

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Degradation of substituted benzoic acids by a Micrococcus species

Cited by 6 publications

References 12 publications

Aerobic Metabolism of 4-Hydroxybenzoic Acid in Archaea via an Unusual Pathway Involving an Intramolecular Migration (NIH Shift)

Aerobic Metabolism of 4-Hydroxybenzoic Acid in Archaea via an Unusual Pathway Involving an Intramolecular Migration (NIH Shift)

Biodegradation of bisphenol A and other bisphenols by a gram-negative aerobic bacterium

Metabolic pathway of homophthalic acid in Pseudomonas alcaligenes

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