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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Peroxisomes01:24

Peroxisomes

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Peroxisomes are specialized organelles present in fungi, plant, and animal cells. It can vary in number, size, morphology, and activity depending on the type of tissue and the nutritional state of the cell. For example, cells with active lipid metabolism, such as adipocytes, neurons, and hepatocytes, have more peroxisomes than other cells in the body. Besides their primary role in breaking down complex organic molecules, peroxisomes can also synthesize specific macromolecules and participate in...
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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Updated: Dec 21, 2025

Resin-Assisted Capture Coupled with Isobaric Tandem Mass Tag Labeling for Multiplexed Quantification of Protein Thiol Oxidation
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Hydrogen peroxide reactivity and specificity in thiol-based cell signalling.

Christine C Winterbourn1

  • 1Centre for Free Radical Research, Department of Pathology and Biomedical Science, University of Otago Christchurch, Christchurch, New Zealand.

Biochemical Society Transactions
|May 16, 2020
PubMed
Summary

Reversible thiol protein oxidation is key for cell signaling. This study explores how less reactive proteins are oxidized, even with highly reactive ones like peroxiredoxins present, using localized oxidation and redox relays.

Keywords:
hydrogen peroxideperoxiredoxinsredox signallingthiol oxidation

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Area of Science:

  • Biochemistry
  • Cell Biology
  • Redox Biology

Background:

  • Reversible oxidation of thiol proteins is a crucial cellular signaling mechanism.
  • Hydrogen peroxide (H2O2) often triggers this oxidation process.
  • A key question is how less reactive proteins become oxidized in the presence of highly reactive proteins like peroxiredoxins.

Purpose of the Study:

  • To investigate the mechanisms behind the selective oxidation of thiol proteins.
  • To understand how cellular redox signaling occurs despite the presence of reactive oxygen species scavengers.
  • To elucidate the roles of localized oxidation and redox relays in protein modification.

Main Methods:

  • Review of recent evidence on cellular oxidation mechanisms.
  • Analysis of signaling pathways involving peroxiredoxins.
  • Examination of directed or facilitated oxidation processes for specific protein targets.

Main Results:

  • Oxidation can be highly localized within cellular compartments.
  • Peroxiredoxins can act as redox relays, facilitating signal transmission.
  • Specific mechanisms exist for the directed oxidation of non-reactive thiol proteins.

Conclusions:

  • Localized oxidation and redox relays are key to understanding thiol protein oxidation in cell signaling.
  • These mechanisms explain how specific proteins are targeted for oxidation.
  • Further research is needed to fully elucidate the complexities of redox signaling pathways.