Aralkyl Hydrodisulfides.<sup>1</sup> III. The Reaction with Tertiary Phosphines

Tsurugi, Jitsuo; Nakabayashi, Takeshige; Ishihara, Tetsuo

doi:10.1021/jo01019a047

Cited by 23 publications

(18 citation statements)

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“…The major products formed are phosphine sulfide (R 3 P═S) and thiol. 496 Analysis of the reaction products provided evidence that, while the attack can occur at either sulfur atom, attack at the outer sulfur predominates, particularly when the persulfide is sterically hindered. 545 Phosphines have been used to detect persulfides in biological samples (see section 7.3.2).…”

Section: Protein Persulfidationmentioning

confidence: 99%

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: 99%

Chemical Biology of H₂S Signaling through Persulfidation

et al. 2017

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“…The outer sulfur can react with cyanide, thiolates, sulfite [133,135], amines [136], hydroxide [137], and tertiary phosphines [138,139]. Persulfides and cyanide react to form the corresponding thiol and thiocyanate, which, in the presence of ferric ions, forms a colored complex that can be quantified spectrophotometrically.…”

Section: Chemistry and Biology Of Persulfidesmentioning

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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“…The generation of − SCN from cyanolysis (Reaction 1) implies that CN − attacks the terminal sulfane 1 sulfur (assuming a single step process, which is not necessarily the case and discussed below). Previous studies have examined the reaction of other nucleophiles with hydropersulfides and reported that many factors can control the site of nucleophilic attack with both sulfur atoms being possible targets [for example, 50,51,52]. More recently Bailey and coworkers [53] generated an organic hydropersulfide and examined its reaction with various nucleophiles and bases in methylene chloride.…”

Section: Discussionmentioning

confidence: 99%

The chemical biology of hydropersulfides (RSSH): Chemical stability, reactivity and redox roles

Saund

Sosa

Henriquez

et al. 2015

Archives of Biochemistry and Biophysics

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Recent reports indicate the ubiquitous prevalence of hydropersulfides (RSSH) in mammalian systems. The biological utility of these and related species is currently a matter of significant speculation. The function, lifetime and fate of hydropersulfides will be assuredly based on their chemical properties and reactivity. Thus, to serve as the basis for further mechanistic studies regarding hydropersulfide biology, some of the basic chemical properties/reactivity of hydropersulfides were studied. The nucleophilicity, electrophilicity and redox properties of hydropersulfides were examined under biological conditions. These studies indicate that hydropersulfides can be nucleophilic or electrophilic, depending on the pH (i.e. the protonation state) and can act as good one- and two-electron reductants. These diverse chemical properties in a single species make hydropersulfides chemically distinct from other, well-known sulfur containing biological species, giving them unique and potentially important biological function.

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Aralkyl Hydrodisulfides.¹ III. The Reaction with Tertiary Phosphines

Cited by 23 publications

References 0 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

The chemical biology of hydropersulfides (RSSH): Chemical stability, reactivity and redox roles

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Aralkyl Hydrodisulfides.1 III. The Reaction with Tertiary Phosphines

Cited by 23 publications

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Chemical Biology of H2S Signaling through Persulfidation

Chemical Biology of H2S Signaling through Persulfidation

Hydrogen Sulfide and Persulfides Oxidation by Biologically Relevant Oxidizing Species

The chemical biology of hydropersulfides (RSSH): Chemical stability, reactivity and redox roles

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Aralkyl Hydrodisulfides.¹ III. The Reaction with Tertiary Phosphines

Chemical Biology of H₂S Signaling through Persulfidation

Chemical Biology of H₂S Signaling through Persulfidation