Anaerobic metabolism of resorcyclic acids (m-dihydroxybenzoic acids) and resorcinol (1,3-benzenediol) in a fermenting and in a denitrifying bacterium

Kluge, Claudia; Tschech, Andreas; Fuchs, Georg

doi:10.1007/bf00291277

Cited by 77 publications

(77 citation statements)

References 32 publications

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“…After 30 s the formation of a labeled product was observed, which migrated similar to phenylphosphate (an authentic catechylphosphate standard was not available). The cells also rapidly converted [U- 14 C]phenol to a labeled product that comigrated with phenylphosphate. After 3 min of incubation the products accounted for the main labeled spots (not shown).…”

Section: Resultsmentioning

confidence: 99%

“…The gray arrows indicate the open reading frames that were not found in the T. aromatica gene cluster. similar 3-hydroxybenzoate gene cluster contains a second copy of the genes coding for benzoyl-CoA reductase (13,14,28). Hence, at least in this organism a very similar isoenzyme of benzoyl-CoA reductase may act in ring reduction of 3-hydroxybenzoyl-CoA.…”

Section: Discussionmentioning

confidence: 99%

“…1). Resorcinol (1,3-dihydroxybenzene) is reduced to 1,3-dioxocyclohexane in an ATP-independent reaction, followed by hydrolytic cleavage of the alicyclic ring (14) (Fig. 1C).…”

Section: Discussionmentioning

confidence: 99%

“…Other compounds, including 2,3-dihydroxybenzoate (pyrocatechuate), 3,5-dihydroxybenzoate (␣-resorcylate), 2,4-dihydroxybenzoate (␤-resorcylate), 2,6-dihydroxybenzoate (␥-resorcylate), and gentisate (2,5-dihydroxybenzoate), are metabolized differently. 2,4-Dihydroxybenzoate and 2,6-dihydroxybenzoate are decarboxylated to resorcinol (14). 2,3-Dihydroxybenzoate is degraded via catechol by decarboxylation (23).…”

Section: Discussionmentioning

confidence: 99%

“…The expected molecular mass was 57.5 kDa. The enzyme acted not only on 3-hydroxybenzoate (specific activity, 14 Cloning of the 4-hydroxybenzoate-CoA ligase gene and purification and analysis of the recombinant enzyme. Surprisingly, 4-hydroxybenzoate-grown cells also contained protocatechuate-CoA ligase activity, although this ligase was reported not to transform protocatechuate.…”

mentioning

confidence: 99%

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Anaerobic Metabolism of Catechol by the Denitrifying Bacterium Thauera aromatica —a Result of Promiscuous Enzymes and Regulators?

2008

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The anaerobic metabolism of catechol (1,2-dihydroxybenzene) was studied in the betaproteobacterium Thauera aromatica that was grown with CO 2 as a cosubstrate and nitrate as an electron acceptor. Based on different lines of evidence and on our knowledge of enzymes and genes involved in the anaerobic metabolism of other aromatic substrates, the following pathway is proposed. Catechol is converted to catechylphosphate by phenylphosphate synthase, which is followed by carboxylation by phenylphosphate carboxylase at the para position to the phosphorylated phenolic hydroxyl group. The product, protocatechuate (3,4-dihydroxybenzoate), is converted to its coenzyme A (CoA) thioester by 3-hydroxybenzoate-CoA ligase. Protocatechuyl-CoA is reductively dehydroxylated to 3-hydroxybenzoyl-CoA, possibly by 4-hydroxybenzoyl-CoA reductase. 3-Hydroxybenzoyl-CoA is further metabolized by reduction of the aromatic ring catalyzed by an ATP-driven benzoyl-CoA reductase. Hence, the promiscuity of several enzymes and regulatory proteins may be sufficient to create the catechol pathway that is made up of elements of phenol, 3-hydroxybenzoate, 4-hydroxybenzoate, and benzoate metabolism.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

“…1). Resorcinol (1,3-dihydroxybenzene) is reduced to 1,3-dioxocyclohexane in an ATP-independent reaction, followed by hydrolytic cleavage of the alicyclic ring (14) (Fig. 1C).…”

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

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