Oxidation Of Thiols By Copper(II)

Smith, Robert C.; Reed, Villel D.; Hill, W. E.

doi:10.1080/10426509408016396

Cited by 71 publications

(55 citation statements)

References 25 publications

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“…However, the presence of trace of transition metal ions will significantly accelerate thiol autoxidation. Transition metal ions such as Cu 2+ and Fe 3+ not only catalyze autoxidation, but also act as direct oxidants in thiol oxidation 22,36,37,49–52. Given the above, it is clear that transition metal ions had to be avoided to minimize the contribution of alternate routes of thiol oxidation.…”

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

190

144

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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

190

144

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“…[17] There is also a report on the complex formation between copper(II) and glutamic acid. [20] This indicates the involvement of the glutamic and/or glycine moieties in the formation of complex of copper(II). [19] Furthermore, the rates of thiol oxidation processes catalyzed by copper(II) are significantly different for different thiols such as glutathione and cysteine.…”

Section: Gsh Oxidation In the Presence Of Cumentioning

confidence: 98%

The Copper(II)‐Catalyzed Oxidation of Glutathione

Ngamchuea

Batchelor‐McAuley

Compton

2016

Chemistry A European J

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The kinetics and mechanisms of the copper(II)-catalyzed GSH (glutathione) oxidation are examined in the light of its biological importance and in the use of blood and/or saliva samples for GSH monitoring. The rates of the free thiol consumption were measured spectrophotometrically by reaction with DTNB (5,5'-dithiobis-(2-nitrobenzoic acid)), showing that GSH is not auto-oxidized by oxygen in the absence of a catalyst. In the presence of Cu , reactions with two timescales were observed. The first step (short timescale) involves the fast formation of a copper-glutathione complex by the cysteine thiol. The second step (longer timescale) is the overall oxidation of GSH to GSSG (glutathione disulfide) catalyzed by copper(II). When the initial concentrations of GSH are at least threefold in excess of Cu , the rate law is deduced to be -d[thiol]/dt=k[copper-glutathione complex][O ] [H O ] . The 0.5 reaction order with respect to O reveals a pre-equilibrium prior to the rate-determining step of the GSSG formation. In contrast to [Cu ] and [O ], the rate of the reactions decreases with increasing concentrations of GSH. This inverse relationship is proposed to be a result of the competing formation of an inactive form of the copper-glutathione complex (binding to glutamic and/or glycine moieties).

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“…As the color change did not appear in the samples corroding in butlyamine it is probable that copper oxidation is slower in the amine solutions than in alcohols, possibly due to removal of oxygen from the solution by copper catalyzed reaction with the thiol. [26] The brown colour of the amine solution after exposure to copper and thiol is likely to be due to the presence of Cu 2 O particles released during corrosion. These are incorporated into the films grown in other solvents.…”

Section: Amine Reagentsmentioning

confidence: 99%

The Self Assembly of Superhydrophobic Copper Thiolate Films on Copper in Thiol Solutions

Whitley¹,

Newton²,

McHale³

et al. 2016

Nano Online

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It is common to think of thiols as molecules that form self-assembled monolayers on gold or similar metals, they have also been used as corrosion inhibitors on copper and steel, but we show here that if the copper remains in thiol solution corrosion is accelerated and a thick layer of corrosion products with a very rough surface forms. The layer is superhydrophobic; repelling water so effectively that it rolls off leaving the surface completely dry. It is composed of a copper (I) thiolate complex and growth occurs quite rapidly under normal conditions. The film morphology depends upon the solvent and thiol used. The presence of organic amines in the solution leads to the formation of thinner layers by removing corrosion products into solution, allowing the removal of native oxide layers.

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Oxidation Of Thiols By Copper(II)

Cited by 71 publications

References 25 publications

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

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

The Copper(II)‐Catalyzed Oxidation of Glutathione

The Self Assembly of Superhydrophobic Copper Thiolate Films on Copper in Thiol Solutions

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