Chemical structure and biodegradability of halogenated aromatic compounds substituent effects on 1,2-dioxygenation of benzoic acid

Reineke, Walter; Knackmuss, Hans‐Joachim

doi:10.1016/0304-4165(78)90372-0

Cited by 166 publications

(97 citation statements)

References 40 publications

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“…Side chain fl uorination only slightly modified the selectivity of toluate dioxygenation by Pseudomonas putida mt-2. According to a previously established (Reineke and Knackmuss 1978a) but later questioned (Schmidt and Knackmuss 1984) rule, the increasing size of substituen ts in 3-substitu ted benzoates should increase the product ratio of 3-to 5-substiluted 1,2-dihydroxy-2-hydrobcnzoates. With 3-methylbenzoate as a substrate the yield of the 3-methyl-isomer was found to be 90%; according to the rule 3-TFM-bcnzoate generated the pure 3-isomcr without any detectable amounts of the 5~isomer.…”

Section: Discussionmentioning

confidence: 98%

“…Benzoate dioxygenasc and toluate dioxygenase were assayed using whole cells (Reineke and Knackmuss 1978a). 1,2·Dihydroxy-2-hydrobenzoate (DHB) dehydrogenases were assayed as described (Reineke and Knackmuss 1978b) except that phosphate buffer was used (50 mM pH 7.4).…”

Section: Spectroscopical Methodsmentioning

confidence: 99%

“…In Pseudomonas sp. B13 for example dioxygenation rates of fluorobenzoates are decreased to 15 to 50% of that found with the parent compound (Reineke and Knackmuss 1978a); the strong electronegative character of the fluorine atom reduces reaction rates of clectrophilic aromatic substitution. The present investigation with trifluoromethylbenzoatcs describes a similar effect on the cooxidation rates of benzoate by Pseudomonas putida rol-2 (PaW) and by the Gram-positive organism Rhodococcus rubropertjnctlL~ N657 when the trifluoromethyl group occur:; as a substituent.…”

mentioning

confidence: 88%

“…One of these bands (R r = 0.42) was observed when the product of 3-TFM -benzoate cooxidation by Alcaligenes eUlfoplms 89 was similarly methylated. This mutant was blocked in the degradation pathway of benzoate and excreted 1,2-dihydroxy-2-hydrobenzoate (DHB) (Reineke and Knackmuss 1978a). Obviously Ml is a TFM· l ,2-dihydroxy· 2-hydrobenzoate.…”

Section: Fig 2 Possible Products Of Cometabolism Of 3-tfm-benzoate Inmentioning

confidence: 99%

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Bacterial metabolism of side chain fluorinated aromatics: cometabolism of 3-trifluoromethyl(TFM)-benzoate by Pseudomonas putida (arvilla) mt-2 and Rhodococcus rubropertinctus n657

1988

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Section: Discussionmentioning

confidence: 98%

Section: Spectroscopical Methodsmentioning

confidence: 99%

mentioning

confidence: 88%

Section: Fig 2 Possible Products Of Cometabolism Of 3-tfm-benzoate Inmentioning

confidence: 99%

See 2 more Smart Citations

Bacterial metabolism of side chain fluorinated aromatics: cometabolism of 3-trifluoromethyl(TFM)-benzoate by Pseudomonas putida (arvilla) mt-2 and Rhodococcus rubropertinctus n657

1988

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“…The amino and hydroxy naphthalene sulphonic acids are building blocks of azo dyes and the sulphonic acid group confers a xenobiotic character to this class of chemicals (41).…”

Section: Introductionmentioning

confidence: 99%

Degradation of h-acid by free and immobilized cells of Alcaligenes latus

Ms¹,

Mk²,

Gaddad³

et al. 2010

Braz. J. Microbiol.

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Alcaligenes latus, isolated from industrial effluent, was able to grow in mineral salts medium with 50 ppm (0.15 mM) of H-acid as a sole source of carbon. Immobilization of Alcaligenes latus in Ca-alginate and polyurethane foam resulted in cells embedded in the matrices. When free cells and immobilized cells were used for biodegradation studies at concentration ranging from 100 ppm (0.3 mM) to 500 ppm (1.15 mM) degradation rate was enhanced with immobilized cells. Cells immobilized in polyurethane foam showed 100% degradation up to 350 ppm (1.05 mM) and 57% degradation at 500 ppm (1.5 mM). Degradation rate of Ca-alginate immobilized cells was less as compared to that of polyurethane foam immobilized cells.With Ca-alginate immobilized cells 100% degradation was recorded up to 200 ppm (0.6 mM) of H-acid and only 33% degradation was recorded at 500 ppm (1.5 mM) of H-acid. Spectral analysis of the products after H-acid utilization showed that the spent medium did not contain any aromatic compounds indicating H-acid degradation by A. latus.

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Microbial Arene Oxidations

Johnson¹

2004

Organic Reactions

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The metabolism of organic molecules by living organisms is of fundamental interest to biologists, microbiologists, and biochemists. The primary avenue of metabolism in most living organisms is via oxidative pathways. The aromatic hydrocarbons (arenes) are subject to such oxidative degradation; their mammalian and microbial systems have been extensively studied. It is the capacity of certain microorganisms to convert by oxidation arenes into arene cis ‐dihydrodiols that provide the foundation of this chapter. Arenes are subject to a variety of oxidations, but the expression “microbial arene oxidation” is used for the specific oxidation discussed here. The assignment of dihydrodiol configuration and the use of mutant strains of microorganisms laid the groundwork for the development of arene oxidation as a process useful to organic synthesis. Other advances discussed in this chapter led to the development of microbial arene oxidations that are suitable for organic synthesis. Attractive features include: the process is one of a very few that disrupts the aromatic system of arenes; the array of functional groups generated in the dihydrodiol products is useful; the process is highly enantioselective, affording pure enantiomerically pure products in most cases. For this chapter, the literature has been reviewed through 2001.

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Chemical structure and biodegradability of halogenated aromatic compounds substituent effects on 1,2-dioxygenation of benzoic acid

Cited by 166 publications

References 40 publications

Bacterial metabolism of side chain fluorinated aromatics: cometabolism of 3-trifluoromethyl(TFM)-benzoate by Pseudomonas putida (arvilla) mt-2 and Rhodococcus rubropertinctus n657

Bacterial metabolism of side chain fluorinated aromatics: cometabolism of 3-trifluoromethyl(TFM)-benzoate by Pseudomonas putida (arvilla) mt-2 and Rhodococcus rubropertinctus n657

Degradation of h-acid by free and immobilized cells of Alcaligenes latus

Microbial Arene Oxidations

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