Aralkyl hydrodisulfides. X. Reactions with iron salts

Kawamura, Shunichi; Abe, Yasuo; Tsurugi, Jitsuo

doi:10.1021/jo01263a093

Cited by 12 publications

(10 citation statements)

References 2 publications

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“…Importantly, persulfides were unable to oxidize ferrous salts. 530 This contrasts with the behavior of hydrogen peroxide and alkyl hydroperoxides, which oxidize ferrous to ferric ion with concomitant formation of a hydroxyl radical via the Fenton reaction (eq 43). H2O2+Fe2+→HO−+HO•+Fe3+…”

Section: Protein Persulfidationmentioning

confidence: 95%

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Chemical Biology of H₂S Signaling through Persulfidation

et al. 2017

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Signaling by HS is proposed to occur via persulfidation, a posttranslational modification of cysteine residues (RSH) to persulfides (RSSH). Persulfidation provides a framework for understanding the physiological and pharmacological effects of HS. Due to the inherent instability of persulfides, their chemistry is understudied. In this review, we discuss the biologically relevant chemistry of HS and the enzymatic routes for its production and oxidation. We cover the chemical biology of persulfides and the chemical probes for detecting them. We conclude by discussing the roles ascribed to protein persulfidation in cell signaling pathways.

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Section: Protein Persulfidationmentioning

confidence: 95%

“…Exposure of aralkyl persulfides to ferric salts under organic solvents led to the formation of tetrasulfide and ferrous ion, showing that persulfides can be oxidized by ferric ions (eqs 41 and 42). 530 RSSH+Fe3+→RSS•+H++Fe2+ 2RSS•→RSSSSR…”

Section: Protein Persulfidationmentioning

confidence: 99%

Chemical Biology of H₂S Signaling through Persulfidation

et al. 2017

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“…The reaction with one-electron oxidants gives rise to RSS• and can occur through hydrogen atom or electron transfer mechanisms [164]. Persulfides can be oxidized by ferric ions and cannot oxidize ferrous ions [166]. Ferricyanide [47], ferric cytochrome c [126,149,167], and metmyoglobin [47] can oxidize persulfides.…”

Section: Reactivity Of Persulfides With Oxidantsmentioning

confidence: 99%

Hydrogen Sulfide and Persulfides Oxidation by Biologically Relevant Oxidizing Species

et al. 2019

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Hydrogen sulfide (H2S/HS–) can be formed in mammalian tissues and exert physiological effects. It can react with metal centers and oxidized thiol products such as disulfides (RSSR) and sulfenic acids (RSOH). Reactions with oxidized thiol products form persulfides (RSSH/RSS–). Persulfides have been proposed to transduce the signaling effects of H2S through the modification of critical cysteines. They are more nucleophilic and acidic than thiols and, contrary to thiols, also possess electrophilic character. In this review, we summarize the biochemistry of hydrogen sulfide and persulfides, focusing on redox aspects. We describe biologically relevant one- and two-electron oxidants and their reactions with H2S and persulfides, as well as the fates of the oxidation products. The biological implications are discussed.

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“…77 Jitsuo Tsurugi later reported that the RSSH oxidative dimerization reaction could also be achieved in high yield in aqueous dioxane using ferric chloride as oxidant (Scheme 5, entry 22). 65 Disulfanyl acetates have remained as popular sources for accessing perthiols to the present time, as they are readily accessible via substitution of thiotosylates (RSTs) with thioacetate ion. 66 In turn, RSTs, when R = alkyl, can be easily synthesised via substitution of RX with thiotosylate ion, 67 while for R = aromatic, RSTs can be accessed via reaction of a disulfide with iodine and sulfinate ion.…”

Section: Review Synopenmentioning

confidence: 99%

A Review of Heterolytic Synthesis Methodologies for Organotri- and Organotetrasulfane Synthesis

Ali

Amer

Petersen

et al. 2021

SynOpen

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It has been ten years since the last comprehensive review on polysulfanes, and during the intervening period, organodi-, organotri- and organotetrasulfanes have featured prominently in both the chemistry and biology literature. This timely update presents both a mechanistic and historical account of synthesis methodology available for organotri- and organotetrasulfanes involving heterolytic S–S bond formation.

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Aralkyl hydrodisulfides. X. Reactions with iron salts

Cited by 12 publications

References 2 publications

Chemical Biology of H₂S Signaling through Persulfidation

Chemical Biology of H₂S Signaling through Persulfidation

Hydrogen Sulfide and Persulfides Oxidation by Biologically Relevant Oxidizing Species

A Review of Heterolytic Synthesis Methodologies for Organotri- and Organotetrasulfane Synthesis

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Aralkyl hydrodisulfides. X. Reactions with iron salts

Cited by 12 publications

References 2 publications

Chemical Biology of H2S Signaling through Persulfidation

Chemical Biology of H2S Signaling through Persulfidation

Hydrogen Sulfide and Persulfides Oxidation by Biologically Relevant Oxidizing Species

A Review of Heterolytic Synthesis Methodologies for Organotri- and Organotetrasulfane Synthesis

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Product

Resources

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Chemical Biology of H₂S Signaling through Persulfidation

Chemical Biology of H₂S Signaling through Persulfidation