Anaerobic O-Demethylations of Methoxynaphthols, Methoxyfuran, and Fluoroanisols bySporomusa ovata

Stupperich, Erhard; Konle, Ralph; Eckerskorn, Christoph

doi:10.1006/bbrc.1996.0971

Cited by 16 publications

(7 citation statements)

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“…From experiments with growing cells and cell extracts of these organism, it is known that A. dehalogenans has the ability to demethylate a wide range of phenyl methyl ethers in addition to the growth substrates used (14,25). Similar observations were described for other homoacetogenic bacteria, such as Sporomusa ovata (52,53) and Moorella thermoacetica (11,63). The O-demethylases of A. dehalogenans are organized in different operons containing the genes for MT II, CP, and MT I.…”

Section: Discussionmentioning

confidence: 59%

The Ether-Cleaving Methyltransferase System of the Strict Anaerobe Acetobacterium dehalogenans : Analysis and Expression of the Encoding Genes

Schilhabel

Studenik

Vödisch³

et al. 2009

J Bacteriol

102

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Section: Discussionmentioning

confidence: 59%

The Ether-Cleaving Methyltransferase System of the Strict Anaerobe Acetobacterium dehalogenans : Analysis and Expression of the Encoding Genes

Schilhabel

Studenik

Vödisch³

et al. 2009

J Bacteriol

102

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“…These bacteria only utilize the methyl group of the substrate for growth and excrete the demethylated aromatic scaffold into the medium (reviewed by Stupperich, 1993;White et al, 1996). O-demethylation of 3,4-dimethoxybenzoate and other methoxy-substituted aromatic compounds has been demonstrated in cell-free extracts of S. ovata and A. woodii (Berman and Frazer, 1992;Stupperich and Konle, 1993;Stupperich et al, 1996). The methyl group is transferred onto tetrahydrofolate (H,folate) by a corrinoid enzyme (Berman and Frazer, 1992;Stupperich and Konle, 1993;Eqn 18); the oxygen atom remains at the aromatic ring (DeWeerd et al, 1988).…”

Section: -Demethylation Compounds Containing Phenyl-methylmentioning

confidence: 99%

Anaerobic Metabolism of Aromatic Compounds

Heider

Fuchs

1997

European Journal of Biochemistry

285

214

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Aromatic compounds comprise a wide variety of low-molecular-mass natural compounds (amino acids, quinones, flavonoids, etc.) and biopolymers (lignin, melanin). They are almost exclusively degraded by microorganisms. Aerobic aromatic metabolism is characterised by the extensive use of molecular oxygen. Monoxygenases and dioxygenases are essential for the hydroxylation and cleavage of aromatic ring structures. Accordingly, the characteristic central intermediates of the aerobic pathways (e.g. catechol) are readily attacked oxidatively. Anaerobic aromatic catabolism requires, of necessity, a quite different strategy. The basic features of this metabolism have emerged from studies on bacteria that degrade soluble aromatic substrates to CO, in the complete absence of molecular oxygen.Essential to anaerobic aromatic metabolism is the replacement of all the oxygen-dependent steps by an alternative set of novel reactions and the formation of different central intermediates (e.g. benzoylCoA) for breaking the aromaticity and cleaving the ring; notably, in anaerobic pathways, the aromatic ring is reduced rather than oxidised. The two-electron reduction of benzoyl-CoA to a cyclic diene requires the cleavage of two molecules of ATP to ADP and P, and is catalysed by benzoyl-CoA reductase. After nitrogenase, this is the second enzyme known which overcomes the high activation energy required for reduction of a chemically stable bond by coupling electron transfer to the hydrolysis of ATP. The alicyclic product cyclohex-I ,5-diene-l-carboxyl-CoA is oxidised to acetyl-CoA via a modified P-oxidation pathway ; the ring structure is opened hydrolytically. Some phenolic compounds are anaerobically transformed to resorcinol (1,3-dihydroxybenzene) or phloroglucinol (1,3,5-trihydroxybenzene). These intermediates are also first reduced and then as alicyclic products oxidised to acetyl-CoA.This review gives an outline of the anaerobic pathways which allow bacteria to utilize aromatics even in the absence of oxygen. We focus on previously unknown reactions and on the enzymes characteristic for such novel metabolism.Keywords ; aromatic metabolism ; benzoyl-CoA ; anaerobic bacteria ; aromatic-ring reduction ; phloroglucinol; resorcinol.This review deals with the art of degrading aromatic compounds to CO, in the complete absence of molecular oxygen. This ability allows bacteria to make use of natural compounds of this widespread class as substrates for growth under anoxic conditions. In nature, anoxic conditions are created when oxygen consumption exceeds its supply. This situation prevails in many environments, e.g. in the intestinal tract of animals and man, in the sediments of all natural bodies of water, in ground water and in part in soil. Aromatic compounds are produced or transformed by all organisms, plants being the most prolific producers. There are numerous low-molecular-mass aromatic compounds includ-

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“…Little is known about the biodegradation of such compounds in anaerobic conditions. Sporomusa ovata metabolizes veratric acid aerobically [15], while Sphingomonas paucimobilis SYK-6 can use syringic acid [16] as a carbon source, and Clostridium methoxyvorans sp. nov. uses syringic acid and 3,4,5-trimethoxybenzoic acid [17] for its growth.…”

Section: Introductionmentioning

confidence: 99%

Structure—biodegradation correlation of polyphenols forThauera aromaticain anaerobic conditions

Dibenedetto

Noce

Narracci

et al. 2006

Chemistry and Ecology

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The anaerobic degradation of phenolic compounds depends greatly on their molecular structure. We have undertaken a systematic study on several phenol derivatives which are commonly found in industrial waters with the aim of investigating the structure-biodegradation relationship for bacteria in anaerobic conditions. The Thauera aromatica strain was used; this bacterium is able to use phenol as a sole carbon source in liquid cultures in the absence of molecular oxygen. Nitrate is the electron sink with complete reduction to N 2 . A systematic study has demonstrated the ability of this bacterial strain to use 3,4-dihydroxybenzoic acid, 4-hydroxycinnamic acid (p-coumaric acid), 4-hydroxy-3-methoxycinnamic acid (ferulic acid), 3,4-dimethoxybenzoic acid (veratric acid), and 3,4,5-trihydroxybenzoic acid (gallic acid) as substrate. The matching of the depletion of the concentration of such compounds with the increment in bacterial growth in the cultures demonstrates that the substrates are used as the sole carbon source. Also, a correlation between the rate of growth of bacteria and nitrite concentration has been observed. The progressive reduction in nitrate into nitrite and N 2 is monitored through analyses. The protein pattern extracted from bacteria grown on methylated substrates is now being compared with that of bacteria grown on non-methylated polyphenols that are structurally analogous in order to identify specific enzymes for demethylation processes.

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Anaerobic O-Demethylations of Methoxynaphthols, Methoxyfuran, and Fluoroanisols bySporomusa ovata

Cited by 16 publications

References 0 publications

The Ether-Cleaving Methyltransferase System of the Strict Anaerobe Acetobacterium dehalogenans : Analysis and Expression of the Encoding Genes

The Ether-Cleaving Methyltransferase System of the Strict Anaerobe Acetobacterium dehalogenans : Analysis and Expression of the Encoding Genes

Anaerobic Metabolism of Aromatic Compounds

Structure—biodegradation correlation of polyphenols forThauera aromaticain anaerobic conditions

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