Sulfones and Sulfoxides

Roy, Kathrin‐Maria

doi:10.1002/14356007.a25_487

Cited by 17 publications

(12 citation statements)

References 141 publications

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“…Sulfides are known to be oxidized by 30% hydrogen peroxide to sulfoxides or sulfones [10,11], and thiol-conjugates of DON are conveniently oxidized to their sulfoxides using this approach without further oxidation to sulfones [6,8]. Oxidation with hydrogen peroxide followed by LC-MS analysis may thus be applied as a simple technique to verify putative DON–thiol conjugates in complex mixtures, an approach analogous to that developed for identifying Met-containing peptides in cyanobacterial blooms [12].…”

Section: Resultsmentioning

confidence: 99%

Glutathione-Conjugates of Deoxynivalenol in Naturally Contaminated Grain Are Primarily Linked via the Epoxide Group

Uhlig

Stanic

Hofgaard

et al. 2016

Toxins

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A glutathione (GSH) adduct of the mycotoxin 4-deoxynivalenol (DON), together with a range of related conjugates, has recently been tentatively identified by LC-MS of DON-treated wheat spikelets. In this study, we prepared samples of DON conjugated at the 10- and 13-positions with GSH, Cys, CysGly, γ-GluCys and N-acetylcysteine (NAC). The mixtures of conjugates were used as standards for LC-HRMS analysis of one of the DON-treated wheat spikelet samples, as well as 19 Norwegian grain samples of spring wheat and 16 grain samples of oats that were naturally-contaminated with DON at concentrations higher than 1 mg/kg. The artificially-contaminated wheat spikelets contained conjugates of GSH, CysGly and Cys coupled at the olefinic 10-position of DON, whereas the naturally-contaminated harvest-ripe grain samples contained GSH, CysGly, Cys, and NAC coupled mainly at the 13-position on the epoxy group. The identities of the conjugates were confirmed by LC-HRMS comparison with authentic standards, oxidation to the sulfoxides with hydrogen peroxide, and examination of product-ion spectra from LC-HRMS/MS analysis. No γ-GluCys adducts of DON were detected in any of the samples. The presence of 15-O-acetyl-DON was demonstrated for the first time in Norwegian grain. The results indicate that a small but significant proportion of DON is metabolized via the GSH-conjugation pathway in plants. To our knowledge, this is the first report of in vivo conjugation of trichothecenes via their epoxy group, which has generally been viewed as unreactive. Because conjugation at the 13-position of DON and other trichothecenes has been shown to be irreversible, this type of conjugate may prove useful as a biomarker of exposure to DON and other 12,13-epoxytrichothecenes.

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Section: Resultsmentioning

confidence: 99%

Glutathione-Conjugates of Deoxynivalenol in Naturally Contaminated Grain Are Primarily Linked via the Epoxide Group

Uhlig

Stanic

Hofgaard

et al. 2016

Toxins

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“…Dimethyl sulfoxide (DMSO) is a widely used dipolar aprotic solvent for both the chemical industry and academic research because of its desirable physical properties that solubilize both organic and inorganic compounds . On industrial scale, DMSO is produced from dimethyl sulfide, a byproduct from the Kraft process for making paper from wood pulp, by oxidation with oxygen or nitrogen dioxide . The DMSO market is poised to reach over $150 million by the year 2025 because of continued increase of worldwide demand, especially driven by the pharmaceutical industry…”

Section: Introductionmentioning

confidence: 99%

Potential Explosion Hazards Associated with the Autocatalytic Thermal Decomposition of Dimethyl Sulfoxide and Its Mixtures

Sheng

Tucker

et al. 2020

Org. Process Res. Dev.

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Dimethyl sulfoxide (DMSO) is widely used as a solvent for chemical reactions, as a cosolvent for crop protection formulations, and in medicines for topical administration of drugs. The potential explosion hazards associated with thermal decomposition of DMSO have been well-documented, with early reports dating back to the late 1950s. However, these explosion hazards are still underappreciated and inadequately communicated, as indicated by the fact that numerous severe accidents have occurred on both laboratory and industrial scales over the years. Differential scanning calorimetry studies show that decomposition of pure DMSO is detected at ca. 278 °C, while accelerating rate calorimetry analysis indicates that thermal decomposition of DMSO occurs at temperatures around its boiling point of 189 °C. Studies also show that the presence of certain substances can significantly lower the onset temperature of DMSO decomposition and also potentially increase the severity of the decomposition reaction through autocatalytic behavior. Further analysis of literature information indicates that there is a wide range of substances that exacerbate the thermal decomposition of DMSO, including acids, bases, halides, metals, electrophiles, oxidants, and reductants. This comprehensive review of explosion hazards associated with the thermal decomposition of DMSO and its mixtures will serve as an educational resource to alert researchers about the need to mitigate these hazards and to incentivize research toward its replacement with safer and greener solvents in the broader chemistry community.

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“… 30 In addition, cellulose can be dissolved in DMSO in the presence of electrolytes, such as tetrabutylammonium acetate 31 and fluoride. 32 DMSO is produced from dimethyl sulfide, 33 a byproduct of the Kraft process used for cellulose pulping, thus being a sustainable solvent. DMSO itself has relatively low toxicity; however, it should be noted that it penetrates skin, thus allowing solutes to pass into the living organism.…”

Section: Introductionmentioning

confidence: 99%

A Fast Dissolution Pretreatment to Produce Strong Regenerated Cellulose Nanofibers via Mechanical Disintegration

Sirviö

Lakovaara

2021

Biomacromolecules

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This study investigates a fast dissolution and regeneration pretreatment to produce regenerated cellulose nanofibers (RCNFs) via mechanical disintegration. Two cellulose pulps, namely, birch and dissolving pulps, with degree of polymerizations of 1800 and 3600, respectively, were rapidly dissolved in dimethyl sulfoxide (DMSO) by using tetraethylammonium hydroxide (TEAOH) as aqueous electrolyte at room temperature. When TEAOH (35 wt % in water) was added to the pulp–DMSO dispersion (pulp:DMSO and TEAOH:DMSO weight ratios of 1:90 and 1:9, respectively), 95% of the dissolving pulp and 85% of the birch pulp fibers dissolved almost immediately. Addition of water caused the regeneration of cellulose without any chemical modification and only a minor decrease of DP, whereas the crystallinity structure of cellulose transformed from cellulose I to cellulose II. The regenerated cellulose could then be mechanically disintegrated into nanosized fibers with only a few passes through a microfluidizer, and RCNF showed fibrous structure. The specific tensile strength of the film produced from both RCNFs exceeded 100 kN·m/kg, and overall mechanical properties of RCNF produced from birch pulp were in line with reference CNF produced by using extensive mechanical disintegration. Although the thermal stability of RCNFs was slightly lower compared to their corresponding original cellulose pulp, the onset temperature of degradation of RCNFs was over 270 °C.

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Sulfones and Sulfoxides

Cited by 17 publications

References 141 publications

Glutathione-Conjugates of Deoxynivalenol in Naturally Contaminated Grain Are Primarily Linked via the Epoxide Group

Glutathione-Conjugates of Deoxynivalenol in Naturally Contaminated Grain Are Primarily Linked via the Epoxide Group

Potential Explosion Hazards Associated with the Autocatalytic Thermal Decomposition of Dimethyl Sulfoxide and Its Mixtures

A Fast Dissolution Pretreatment to Produce Strong Regenerated Cellulose Nanofibers via Mechanical Disintegration

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