Peroxidase-Catalyzed Desulfonation of 3,5-Dimethyl-4-hydroxy and 3,5-Dimethyl-4-aminobenzenesulfonic Acids

Muralikrishna, C.; Renganathan, V.

doi:10.1006/bbrc.1993.2549

Cited by 22 publications

(13 citation statements)

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“…This result is in agreement with the results found by Muralikrishna and Renganathan (1993) for the desulfonation of a hydroxy-amino-substituted benzen-sulfonic acid by LiP from P. chrysosporium. They concluded that the peroxidases might be involved in the desulfonation of aromatic rings, thus preparing them for further degradation.…”

Section: Color and Phsupporting

confidence: 94%

“…In the IC analysis, we noticed an increase in the level of sulfate in the culture filtrate, while in FTIR analysis we observed evidence of sulfonic groups removal. It is safe to postulate that the sulfonic groups were gradually separated from the carbon structure (result similar to that obtained by Muralikrishna and Renganathan 1993). Also, the FTIR signals associated with the two naphthalenic rings resulting after azo link breakage (naphthalene sulfonate VII and 3,7 sulfonate-1,2-naphthoquinone VIII) did not disappear completely.…”

Section: Dialysismentioning

confidence: 50%

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Chemical evidence for the mechanism of the biodecoloration of Amaranth by Trametes versicolor

Gavril

Hodson

2006

World J Microbiol Biotechnol

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The white-rot fungus Trametes versicolor decolorized Amaranth. The hypothesis that the carbon structure of Amaranth was broken down in smaller mass fragments was investigated analyzing the products of decoloration. FTIR spectroscopy, ion chromatography, sulfite and ammonia analysis were used to compare the culture filtrate before dye addition, with the pure dye, the culture filtrate after dye addition, and the culture filtrate during the treatment. The hypothesis of polymerization of the decoloration products was tested by spectrophotometric analysis of dialysates of the pure dye, the culture filtrate before dye addition, and the culture filtrates after dye addition and decoloration. FTIR showed that the signals typical for the azo group disappeared after decoloration, while new peaks appeared that were characteristic of substituted naphthalenic or benzenic compounds. Ion chromatography showed that the level of sulfate in the treatment increased when compared with the level of the sulfate in control, suggesting that the sulfonic groups were being stripped from Amaranth's structure and metabolized to sulfate. Sulfite measurements for the treatment and controls showed no significant difference, and were well below the saturation concentration for sulfite in water, confirming that the medium was aerobic. Ammonia concentration did not change with the decoloration. Absorbance scans after dialysis of decolorized samples showed no new peaks, suggesting that the decoloration products were not polymerized. These observations suggests that the decoloration mechanism starts with the azo link removal, followed by desulfonation, naphthalene ring opening, and the formation of smaller mass fragments, similar to fungal metabolites.

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Section: Color and Phsupporting

confidence: 94%

Section: Dialysismentioning

confidence: 50%

Chemical evidence for the mechanism of the biodecoloration of Amaranth by Trametes versicolor

Gavril

Hodson

2006

World J Microbiol Biotechnol

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“…Desulfonations of aromatic sulfonates in fungi have also been implied, because CO P from the ring carrying the sulfonate was released [112], or observed directly [113]. These reactions have been attributed to (extracellular) peroxidases [113,114], which sometimes lead to extensive destruction of the compounds involved, essentially as in the enzymic combustion of lignin [115].…”

Section: Fungal Peroxidases and Arenesulfonatesmentioning

confidence: 99%

“…These reactions have been attributed to (extracellular) peroxidases [113,114], which sometimes lead to extensive destruction of the compounds involved, essentially as in the enzymic combustion of lignin [115]. In these cases, no transport of the sulfonate is required, because the fungus has already exported the non-speci¢c peroxidase.…”

Section: Fungal Peroxidases and Arenesulfonatesmentioning

confidence: 99%

Microbial desulfonation

Cook

1998

FEMS Microbiology Reviews

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Organosulfonates are widespread compounds, be they natural products of low or high molecular weight, or xenobiotics. Many commonly found compounds are subject to desulfonation, even if it is not certain whether all the corresponding enzymes are widely expressed in nature. Sulfonates require transport systems to cross the cell membrane, but few physiological data and no biochemical data on this topic are available, though the sequences of some of the appropriate genes are known. Desulfonative enzymes in aerobic bacteria are generally regulated by induction, if the sulfonate is serving as a carbon and energy source, or by a global network for sulfur scavenging (sulfate starvation induced (SSI) stimulon) if the sulfonate is serving as a source of sulfur. It is unclear whether an SSI regulation is found in anaerobes. The anaerobic bacteria examined can express the degradative enzymes constitutively, if the sulfonate is being utilized as a carbon source, but enzyme induction has also been observed. At least three general mechanisms of desulfonation are recognisable or postulated in the aerobic catabolism of sulfonates: (1) activate the carbon neighboring the C y Q bond and release of sulfite assisted by a thiamine pyrophosphate cofactor; (2) destabilize the C y Q bond by addition of an oxygen atom to the same carbon, usually directly by oxygenation, and loss of the good leaving group, sulfite; (3) an unidentified, formally reductive reaction. Under SSIS control, different variants of mechanism (2) can be seen. Catabolism of sulfonates by anaerobes was discovered recently, and the degradation of taurine involves mechanism (1). When anaerobes assimilate sulfonate sulfur, there is one common, unknown mechanism to desulfonate the inert aromatic compounds and another to desulfonate inert aliphatic compounds; taurine seems to be desulfonated by mechanism (1).

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“…Several physicochemical and biological techniques have been investigated [8,11,12] Figure 1. The structures of the five sulphonated anthraquinones for which the CE procedure was developed.…”

Section: Introductionmentioning

confidence: 99%

Capillary electrophoretic separation of sulphonated anthraquinones in a variety of matrices

Aubert

Schwitzguébel

2002

Chromatographia

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SummarySulphonated anthraquinones are resistant to biodegradation and are, therefore, not eliminated by traditional wastewater treatment plants; this leads to their accumulation in fresh water. To develop new technologies, e.g. phytoremediation, for treatment of such pollutants, a powerful technique is needed for their rapid and inexpensive detection and quantification in any kind of sample. For this purpose capillary electrophoresis seems to be a very promising technique.An efficient, rapid, and inexpensive method has been developed for analysis of five sulphonated anthraquinones, in the 50-950 IxM range, with a simple borate buffer. The procedure has been shown to be efficient for all the samples tested, i.e. pure standard solutions, hydroponic media in which plants, bacteria, and algae had grown for 6 weeks, and even plant extracts. This last result is consistent with the idea that phytoremediation could be used as an alternative means ofwastewater treatment for these recalcitrant compounds.

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Peroxidase-Catalyzed Desulfonation of 3,5-Dimethyl-4-hydroxy and 3,5-Dimethyl-4-aminobenzenesulfonic Acids

Cited by 22 publications

References 0 publications

Chemical evidence for the mechanism of the biodecoloration of Amaranth by Trametes versicolor

Chemical evidence for the mechanism of the biodecoloration of Amaranth by Trametes versicolor

Microbial desulfonation

Capillary electrophoretic separation of sulphonated anthraquinones in a variety of matrices

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