The Oxidation of cysteine by Iron and Hydrogen Peroxide

Neville, Roy G.

doi:10.1021/ja01567a028

Cited by 22 publications

(9 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Studies performed with glutathione (GSH) in a pH range (3–7) have shown that Fe(II) is spontaneously produced when GSH is added to Fe(III) (Figure ). , The same has been shown with Cys at low pH, because the Fe(III)–Cys complex is unstable and quickly reacts to yield Fe(II) and cystine . Previous work has failed to provide evidence of free thiyl radical generation under those conditions, and disulfide is seemingly formed in situ before being released from the metal complex.…”

Section: Introductionmentioning

confidence: 70%

“…15,16 The same has been shown with Cys at low pH, because the Fe(III)−Cys complex is unstable and quickly reacts to yield Fe(II) and cystine. 17 Previous work has failed to provide evidence of free thiyl radical generation under those conditions, 15 and disulfide is seemingly formed in situ before being released from the metal complex. Resulting Fe(II) remains bound to GSSG and is only released when excess GSH is present; however, unlike Cu(I), which coordinates strongly with thiols, Mossbauer spectroscopy showed that Fe(II) is not bound to sulfur.…”

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Reaction Mechanisms of Metals with Hydrogen Sulfide and Thiols in Model Wine. Part 2: Iron- and Copper-Catalyzed Oxidation

Kreitman

Danilewicz²,

Jeffery

et al. 2016

J. Agric. Food Chem.

View full text Add to dashboard Cite

Sulfidic off-odors arising during wine production are frequently removed by Cu(II) fining. In part 1 of this study ( 10.1021/acs.jafc.6b00641 ), the reaction of H2S and thiols with Cu(II) was examined; however, the interaction of iron and copper is also known to play an important synergistic role in mediating non-enzymatic wine oxidation. The interaction of these two metals in the oxidation of H2S and thiols (cysteine, 3-sulfanylhexan-1-ol, and 6-sulfanylhexan-1-ol) was therefore examined under wine-like conditions. H2S and thiols (300 μM) were reacted with Fe(III) (100 or 200 μM) alone and in combination with Cu(II) (25 or 50 μM), and concentrations of H2S and thiols, oxygen, and acetaldehyde were monitored over time. H2S and thiols were shown to be slowly oxidized in the presence of Fe(III) alone and were not bound to Fe(III) under model wine conditions. However, Cu(II) added to model wine containing Fe(III) was quickly reduced by H2S and thiols to form Cu(I) complexes, which then rapidly reduced Fe(III) to Fe(II). Oxidation of Fe(II) in the presence of oxygen regenerated Fe(III) and completed the iron redox cycle. In addition, sulfur-derived oxidation products were observed, and the formation of organic polysulfanes was demonstrated.

show abstract

Section: Introductionmentioning

confidence: 70%

Section: ■ Introductionmentioning

confidence: 99%

Reaction Mechanisms of Metals with Hydrogen Sulfide and Thiols in Model Wine. Part 2: Iron- and Copper-Catalyzed Oxidation

Kreitman

Danilewicz²,

Jeffery

et al. 2016

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…The reaction between CSH and H 2 O 2 has been previously studied by several other groups 10,14,43,45. Normally in these studies, the concentrations of thiol and H 2 O 2 were measured by colorimetric methods and CSSC concentration was not analyzed.…”

Section: Resultsmentioning

confidence: 99%

Kinetics and Mechanism of the Reaction of Cysteine and Hydrogen Peroxide in Aqueous Solution

Luo

Smith

Anderson

2005

Journal of Pharmaceutical Sciences

199

144

View full text Add to dashboard Cite

“…Although hydrogen peroxide has been predicted as a product of this reaction, hydrogen peroxide has not been demonstrated as a stable product of the reaction (37,50). One reason could be that hydrogen peroxide reacts with cysteine (38,43,51). The finding in the present study that catalase was inhibited in the presence of 3-amino-1,2,4-triazole in an autoxidizing solution of cysteine (Fig.…”

Section: -mentioning

confidence: 99%

Bactericidal effect of cysteine exposed to atmospheric oxygen

Carlsson¹,

Granberg²,

Nyberg³

et al. 1979

Appl Environ Microbiol

View full text Add to dashboard Cite

Peptostreptococcus anaerobius VPI 4330-1 was exposed to atmospheric oxygen in a dilution blank (0.2% gelatin, salts, resazurin) solution. The organisms were rapidly killed when the solution contained cysteine. The organisms were effectively protected by catalase and horseradish peroxidase as well as by the metal ion-chelating agents 8-hydroxyquinoline and 2,2'-bipyridine. Superoxide dismutase increased the rate of killing of the organisms, whereas singlet oxygen quenchers and scavengers of hydroxyl free radicals did not protect the organisms from the toxic effect of cysteine. Hydrogen peroxide was formed when cysteine was exposed to oxygen in the dilution blank solution, and the reaction was inhibited by metal ion-chelating agents. The organisms were rapidly killed by 20 ,uM hydrogen peroxide in anaerobic dilution blank solution. The toxic effect of hydrogen peroxide was completely abolished by catalase and metal ion-chelating agents. These results indicated that hydrogen peroxide was formed in the dilution blank solution in a metal ion-catalyzed autoxidation of cysteine and that hydrogen peroxide was toxic to P. anaerobius VPI 4330-1 in a reaction also catalyzed by metal ions. Cysteine may be toxic to or may inhibit growth of Escherichia coli (11, 25, 46), Bacillus subtilis (52), yeasts (7, 33, 36), and fungi (4, 49). Cysteine appears to inhibit growth by two different mechanisms in E. coli. It may interfere with biosynthesis of leucine, isoleucine, threonine, and valine, or it may interact with the function of membrane-bound enzymes (25). The growth-inhibiting effect of cysteine in yeasts has been ascribed to its ability to chelate metal ions necessary for the activities of various enzymes (7, 36). Cysteine is routinely used in many media for the cultivation of anaerobic bacteria (22). In a study on the bactericidal effects of various culture media exposed to atmospheric oxygen (13), it was observed that cysteine was toxic to Peptostreptococcus anaerobius VPI 4330-1. We now report that hydrogen peroxide is formed from cysteine in the presence of oxygen in a metal ion-catalyzed reaction and that hydrogen peroxide is toxic to P. anaerobius VPI 4330-1 in a reaction also catalyzed by metal ions. MATERIALS AND METHODS Microorganisms. P. anaerobius strain VPI 4330-1 (ATCC 27337) was used as the test strain (23). It was kept on blood agar plates at 4°C under strictly anaerobic conditions in an anaerobic box with an atmosphere of 10% H2 and 5% CO2 in nitrogen (54).

show abstract

The Oxidation of cysteine by Iron and Hydrogen Peroxide

Cited by 22 publications

References 0 publications

Reaction Mechanisms of Metals with Hydrogen Sulfide and Thiols in Model Wine. Part 2: Iron- and Copper-Catalyzed Oxidation

Reaction Mechanisms of Metals with Hydrogen Sulfide and Thiols in Model Wine. Part 2: Iron- and Copper-Catalyzed Oxidation

Kinetics and Mechanism of the Reaction of Cysteine and Hydrogen Peroxide in Aqueous Solution

Bactericidal effect of cysteine exposed to atmospheric oxygen

Contact Info

Product

Resources

About