The Oxidation of Cystine in Non-Aqueous Media

Toennies, Gerrit; Lavine, Theodore F.

doi:10.1016/s0021-9258(18)74877-1

Cited by 62 publications

(14 citation statements)

References 9 publications

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“…The sulfur-sulfur bond in cystine "disulfoxide" is cleaved in acid solution (185) to give cysteinesulfinic acid and the reactive sulfenium ion (15). 0 RS-SR + H+ <=t RS+ + RS02H (17) 0 Electrophilic scission of the sulfur-sulfur bond (equation 18) has been postulated for the acid-base catalyzed reactions of dimethylformamide with carboxylsubstituted alkyl disulfides related to cystine (157).…”

Section: Rssr 2rs• (4)mentioning

confidence: 99%

The Scission Of The Sulfur-Sulfur Bond

Parker¹,

Kharasch²

1959

Chem. Rev.

324

152

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Section: Rssr 2rs• (4)mentioning

confidence: 99%

The Scission Of The Sulfur-Sulfur Bond

Parker¹,

Kharasch²

1959

Chem. Rev.

324

152

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“…(2) Scarpa, Atti Acad. Lincei, [5] dull red heat, a weight loss of 12.5% was found. It was assumed that the only impurity present in significant amount after dehydration was the 1% of carbonate.…”

Section: Research Laboratoriesmentioning

confidence: 95%

“…358.7 365.0 365.0 366.9 366. 5 By extrapolation, the freezing point of potassium hydroxide with no carbonate present was estimated to be 410°. A transition which Hevesy found at 248°and Scarpa at 360°was found at 249°.…”

Section: Research Laboratoriesmentioning

confidence: 99%

The Melting Point of Potassium Hydroxide

Seward¹,

Martin²

1949

J. Am. Chem. Soc.

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“…Disulfides and thiols can be easily oxidized to sulfinates and sulfonates, including copper ions (Cu 2+ ) as catalyst. Autoxidation of disulfides (RSSR) and disulfoxides (RSOSOR) in alkaline solutions (reaction 1 and 2), or dismutation of disulfoxides (reaction 3), gives rise to sulfinates according to these reactions [54]:…”

Section: Sulfinates and Sulfonates (Cysteine/homocysteine Sulfinic Ac...mentioning

confidence: 99%

“…Cysteine sulfinic acid: The sulfinate is prepared from cystine disulfoxide according to Lavine [54]. Cystine disulfoxide: 1.2 g (4.4 mmol) of cystine is transferred in a 0.2 L flask with 25 mL of acetonitrile.…”

Section: Rssh + Hmentioning

confidence: 99%

Chemistry of Outlandish Natural Products Belonging to Sulfur Metabolism: Unrevealed Green Syntheses and Separation Strategies from the Cavallini’s Old School

2022

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The last century has been very important from the point of view of research and investigation in the fields of the chemistry and biochemistry of sulfur-containing natural products. One of the most important contributions to the discovery and study of human sulfur-containing metabolites was performed by the research group of Professor Doriano Cavallini at Sapienza University of Rome, during the last 80 years. His research brought to light the discovery of unusual sulfur metabolites that were chemically synthesized and determined in different biological specimens. Most of his synthetical strategies were performed in aqueous conditions, which nowadays can be considered totally in line with the recent concepts of the green chemistry. The aim of this paper is to describe and summarize synthetic procedures, and purification and analytical methods from the Cavallini’s school, with the purpose to provide efficient and green methodologies for the preparation and obtainment of peculiar unique sulfur-containing metabolites.

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The Oxidation of Cystine in Non-Aqueous Media

Cited by 62 publications

References 9 publications

The Scission Of The Sulfur-Sulfur Bond

The Scission Of The Sulfur-Sulfur Bond

The Melting Point of Potassium Hydroxide

Chemistry of Outlandish Natural Products Belonging to Sulfur Metabolism: Unrevealed Green Syntheses and Separation Strategies from the Cavallini’s Old School

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