Hydrogen Sulfide

Dittmer, Donald C.

doi:10.1002/047084289x.rh049

Cited by 5 publications

(9 citation statements)

References 72 publications

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“…Like thiolate (RS − ), HS − is also a nucleophile [56,57] (see 5.1 ). Its nucleophilic reactions with 5,5′-dithiobis-(2-nitrobenzoic acid) [58], N-ethylmaleimide [58], parachloromercuribenzoate [58], 2,2′-dipyridyl disulfide [59] and monobromobimane [45,60,61] have been utilized for H 2 S detection.…”

Section: Basic Physical and Chemical Propertiesmentioning

confidence: 99%

Chemical foundations of hydrogen sulfide biology

2013

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Following nitric oxide (nitrogen monoxide) and carbon monoxide, hydrogen sulfide (or its newer systematic name sulfane, H2S) became the third small molecule that can be both toxic and beneficial depending on the concentration. In spite of its impressive therapeutic potential, the underlying mechanisms for its beneficial effects remain unclear. Any novel mechanism has to obey fundamental chemical principles. H2S chemistry was studied long before its biological relevance was discovered, however, with a few exceptions, these past works have received relatively little attention in the path of exploring the mechanistic conundrum of H2S biological functions. This review calls attention to the basic physical and chemical properties of H2S, focuses on the chemistry between H2S and its three potential biological targets: oxidants, metals and thiol derivatives, discusses the applications of these basics into H2S biology and methodology, and introduces the standard terminology to this youthful field.

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Section: Basic Physical and Chemical Propertiesmentioning

confidence: 99%

Chemical foundations of hydrogen sulfide biology

2013

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“…[17] Using a properly constructed azide, this reduction generates a fluorescent molecule permitting the development of a new group of H 2 S sensors based on this chemistry (Figure 8). [19, 63] Most importantly, H 2 S preferentially reduces these azides compared to cysteine and glutathione making mew H 2 S detectors selective in biological systems.…”

Section: Other H2s Reactionsmentioning

confidence: 99%

“…Both the organic and biological chemical reactivity of H 2 S have been reviewed. [6, 10, 11, 17] The size and electronegativity of the sulfur atom increase the acidity of H 2 S compared to water giving a first pKa of 6.8, which results in about two-thirds of H 2 S existing in the anionic form − SH at pH 7.4 (Figure 1). [6] The second pKa of 14.1 reveals that only small amounts of S −2 exist at pH 7.4.…”

Section: Introductionmentioning

confidence: 99%

“…[6] The polarizability of the sulfur atom makes the sulfide anion ( − SH) an excellent nucleophile that reacts with numerous electrophilic organic substrates. [6, 17] Hydrogen sulfide and the − SH anion reduce a variety of organic substrates. [17] Electrochemical evidence indicates − SH acts as a weaker two electron reducing agent (forming S 0 ) than glutathione and cysteine but the redox potential of H 2 S appears similar to both cysteine and glutathione.…”

Section: Introductionmentioning

confidence: 99%

“…[6, 17] Hydrogen sulfide and the − SH anion reduce a variety of organic substrates. [17] Electrochemical evidence indicates − SH acts as a weaker two electron reducing agent (forming S 0 ) than glutathione and cysteine but the redox potential of H 2 S appears similar to both cysteine and glutathione. [13, 18] Hydrogen sulfide preferentially (compared to cysteine and glutathione) reduces aromatic azides and nitro compounds to the amines forming the basis of new and selective fluorescent H 2 S probes indicating H 2 S acts as a better reducing agent than biological thiols under these conditions.…”

Section: Introductionmentioning

confidence: 99%

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Potential biological chemistry of hydrogen sulfide (H2S) with the nitrogen oxides

King

2013

Free Radical Biology and Medicine

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Hydrogen sulfide, an important gaseous signaling agent generated in numerous biological tissues, influences many physiological processes. This biological profile appears reminiscent of nitric oxide, another important endogenously synthesized gaseous signaling molecule. Hydrogen sulfide reacts with nitric oxide or oxidized forms of nitric oxide and nitric oxide donors in vitro to form species that display distinct biology compared to both hydrogen sulfide and NO. The products of these interesting reactions may include small molecule S-nitrosothiols or nitroxyl, the one-electron reduced form of nitric oxide. In addition, thionitrous acid or thionitrite, compounds structurally analogous to nitrous acid and nitrite may constitute a portion of the reaction products. Both the chemistry and biology of thionitrous acid and thionitrite, compared to nitric oxide or hydrogen sulfide, remain poorly defined. General mechanisms for the formation of S-nitrosothiols, nitroxyl and thionitrous acid based upon the ability of hydrogen sulfide to act as a nucleophile and reducing agent with reactive nitric oxide-based intermediates are proposed. Hydrogen sulfide reactivity appears extensive and could impact numerous areas of redox controlled biology and chemistry warranting more work in this exciting and developing area.

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Synthesis of 2-Oxopropanethioamide for the Manufacture of Lanabecestat: A New Route for Control, Robustness, and Operational Improvements

Taylor

Barrat

Woodward

et al. 2017

Org. Process Res. Dev.

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A new route to 2-oxopropanethioamide, a key intermediate in the synthesis of lanabecestat (AZD3293/LY3314814), is described by employing commercially available 2,2-diethoxypropionitrile as a raw material. In contrast to the previous route, this work offers several advantages; for example, the raw material is safer to manufacture and handle, highly toxic hydrogen sulfide gas is no longer required as a reagent, and in situ FTIR spectroscopy monitoring has provided manufacturing controls and robustness. Additionally, this route offers a hold-and control-point by virtue of an isolable crystalline intermediate, which in turn provides improved quality that is evident in the downstream synthesis. An extensive design-of-experiment analysis was undertaken to understand multifactor interdependencies, build a model, visualize factor relationships, map the process parameter reaction space, identify potential process operating conditions, and predict their performance.

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Hydrogen Sulfide

Cited by 5 publications

References 72 publications

Chemical foundations of hydrogen sulfide biology

Chemical foundations of hydrogen sulfide biology

Potential biological chemistry of hydrogen sulfide (H2S) with the nitrogen oxides

Synthesis of 2-Oxopropanethioamide for the Manufacture of Lanabecestat: A New Route for Control, Robustness, and Operational Improvements

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