Organic Sulfur Compounds. VII. Some Addition and Co-oxidation Reactions of Thiols with 2,5-Dimethyl-2,4-hexadiene

Oswald, Alexis A.; Hudson, Boyd E.; Rodgers, George F.; Noel, Fernand

doi:10.1021/jo01054a037

Cited by 24 publications

(9 citation statements)

References 3 publications

(3 reference statements)

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“…Thought must also be given to the fixation of the carboxyl end of the peptide to a polymeric support by covalent bonds [57,63,641 that can be broken again under mild conditions. In the automatic Edman method the support is the residual molecule itself, which is extracted toward the end.…”

mentioning

confidence: 99%

Problems and Possibilities of the Free‐Radical Addition of Thiols to Unsaturated Compounds

Griesbaum¹

1970

Angew. Chem. Int. Ed. Engl.

359

219

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pletely eliminated in some cases, since much longer chains can now be sequenced than formerly. 2. Because of the good yields in the sequenator and the increased detection sensitivity for amino acids, the quantity of material required for sequence analysis will be considerably reduced. 3. The time required for the actual sequence analysis has already been greatly reduced, and 15 degradation steps can now be carried out in 24 hours. (The determination of the sequence of insulin by the DNP method took Sanger and three coworkers ten years, while Braunitzer and five colleagues, using a greatly improved method, spent six years on the sequencing of hemoglobin. The determination of the sequence of a chain of 150 amino acids by the classical manual Edman method takes two people about two years.) In view of the growing importance of photochemically initiated reactions in industry, the use of free-radical additions of thiols to unsaturated compounds also seems promising. The present article is intended to demonstrate the possibilities and limitations of reactions of this type in organic synthesis.

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mentioning

confidence: 99%

Problems and Possibilities of the Free‐Radical Addition of Thiols to Unsaturated Compounds

Griesbaum¹

1970

Angew. Chem. Int. Ed. Engl.

359

219

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“…The production of radicals from glutathione has been confirmed by EPR studies, but their detection requires trapping agents due to their high instability. − Thiyl radicals can be formed by radical reactions, enzymes, light (with and without the presence of sensitizers), heat and also by metal ions. ,− On the basis of kinetic studies, the production of glutathiyl radicals was proposed in acidic aqueous solutions containing either copper(II) or iron(III) and glutathione, ,,, whereby the metal ions were reduced to copper(I) or iron(II) and glutathione formed a disulfide. Consequently, the presence of metal ions, glutathione and oxygen in the model wine system would appear conducive to glutathiyl radicals, and indeed glutathione disulfides were detected in our previous study .…”

Section: Resultsmentioning

confidence: 99%

A Novel Glutathione-Hydroxycinnamic Acid Product Generated in Oxidative Wine Conditions

Bouzanquet

Barril

Clark

et al. 2012

J. Agric. Food Chem.

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This study characterizes a novel glutathione-substituted dihydroxyphenyl compound formed during the oxidation of white wine and model wine solutions, which may contribute to the synergistic role of glutathione and hydroxycinnamic acids in delaying oxidative coloration. The critical components for the formation of the compound were found to be hydroxycinnamic acids and glutathione, while ascorbic acid enabled the product to accumulate to higher concentrations. The presence of the wine components important in other wine oxidation mechanisms, (+)-catechin, ethanol and/or tartaric acid, was not essential for the formation of this new compound. Via LC-MS/MS, HR-MS and (1)H NMR (1D and 2D NMR) analyses, the major isomer of the compound formed from glutathione and caffeic acid was found to be 4-[(E)-2'-(S)-glutathionyl ethenyl]-catechol (GEC). Equivalent products were also confirmed via LC-MS/MS for other hydroxycinnamic acids (i.e., ferulic and coumaric acids). Only trace amounts of GEC were formed with the quinic ester of caffeic acid (i.e., chlorogenic acid), and no equivalent product was found for cinnamic acid. GEC was detected in a variety of white wines supplemented with glutathione and caffeic acid. A radical mechanism for the formation of the styrene-glutathione derivatives is proposed.

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“…The radical addition of thiol to 2,5dimethyl-2,4-hexadiene forms secondary radicals and tertiary radicals from the resonance stabilization of radicals. However, the main reaction product is 1,2-adduct contrary to their radical stability (Figure 4) 42) .…”

Section: The Radical Reaction Through the Allylic Radicalmentioning

confidence: 97%

“…The addition of a free radical to the diene compound produces the allylic radical and results in several products of structural isomers [36][37][38][39][40][41][42][43][44][45] .…”

Section: The Radical Reaction Through the Allylic Radicalmentioning

confidence: 99%

The Main Mechanism and Cross-Linking Structure for Accelerated Sulfur Vulcanization

Choi

2006

e-J. Soft Mater.

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The reactivities of hydrocarbon, the radical reactions through the allylic radicals, the results of model compound vulcanization, and the cross-link structures of vulcanizates are comprehensively discussed to understand the main reaction for accelerated sulfur vulcanization. Through this review, the author's view on the main mechanism and cross-linking structure for accelerated sulfur vulcanization are discussed.

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Organic Sulfur Compounds. VII. Some Addition and Co-oxidation Reactions of Thiols with 2,5-Dimethyl-2,4-hexadiene

Cited by 24 publications

References 3 publications

Problems and Possibilities of the Free‐Radical Addition of Thiols to Unsaturated Compounds

Problems and Possibilities of the Free‐Radical Addition of Thiols to Unsaturated Compounds

A Novel Glutathione-Hydroxycinnamic Acid Product Generated in Oxidative Wine Conditions

The Main Mechanism and Cross-Linking Structure for Accelerated Sulfur Vulcanization

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