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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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Oxidation of Phenols to Quinones01:17

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In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
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The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
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During the electron transport chain, electrons from NADH and FADH2 are first transferred to complexes I and II, respectively. These two complexes then transfer the electrons to ubiquinol, which carries them further to complex III. Complex III passes the electrons across the intermembrane space to Cyt c, which carries them further to complex IV. Complex IV donates electrons to oxygen and reduces it to water. As electrons pass through complexes I, III, and IV, the energy released aids the pumping...
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Redox Reactions01:27

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Redox reactions are vital biochemical processes that underpin energy metabolism in cells. These reactions involve the transfer of electrons between molecules, occurring in tandem as oxidation and reduction. Oxidation refers to the loss of electrons, while reduction denotes their gain. This coupling ensures the seamless flow of electrons through metabolic pathways. For example, in bacterial metabolism, glucose undergoes oxidation to carbon dioxide, while oxygen is simultaneously reduced to...
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Redox Reactions01:24

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Oxidation-reduction or redox reactions involve the transfer of electrons from one molecule or atom to another. When an atom gains an electron, another atom must lose an electron, meaning oxidation and reduction must occur together. Since the redox occurs in pairs, the atom that gets oxidized is also called the reducing agent or reductant, and the atom that is reduced is also called the oxidizing agent or oxidant. A straightforward way to remember the definitions of oxidation and reduction is...
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Resin-Assisted Capture Coupled with Isobaric Tandem Mass Tag Labeling for Multiplexed Quantification of Protein Thiol Oxidation
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Prooxidative chain transfer activity by thiol groups in biological systems.

Sascha Kunath1, Mario Schindeldecker1, Antonio De Giacomo2

  • 1Evolutionary Biochemistry and Redox Medicine, Institute for Pathobiochemistry, University Medical Center of the Johannes Gutenberg University, Mainz, Germany.

Redox Biology
|September 1, 2020
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Summary

Lipophilic thiols accelerate oxidative damage in biological systems by acting as radical chain transfer agents. This explains the "cysteine anomaly" in protein structures and identifies thiols as potential cytotoxins.

Keywords:
Cysteine oxidationLipid peroxidationProtein oxidationRadical propagationThiyl radicals

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Area of Science:

  • Biochemistry
  • Molecular Biology
  • Cell Biology

Background:

  • Cysteine's thiol group is crucial for protein function but its unusual distribution in proteins (the "cysteine anomaly") remains unexplained.
  • Lipophilic thiols are known radical chain transfer agents in polymer chemistry.

Purpose of the Study:

  • To investigate the hypothesis that lipophilic thiols' radical chain transfer activity explains the cysteine anomaly.
  • To explore the biological effects of lipophilic thiols in various model systems.

Main Methods:

  • Experiments were conducted using isolated biomembranes, cultivated human cells, and the whole animal model Caenorhabditis elegans.
  • The effects of dodecylthiol and related compounds were assessed, focusing on lipid peroxidation, fatty acid isomerization, and cellular stress responses.

Main Results:

  • Lipophilic thiols at micromolar concentrations accelerated lipid peroxidation and catalyzed fatty acid isomerization to trans-fatty acids.
  • These compounds induced significant cellular stress responses, including protein and DNA damage.
  • The observed effects were specific to lipophilic thiols and not seen with thioethers, alcohols, or hydrophilic compounds.

Conclusions:

  • The catalytic chain transfer activity of thiyl radicals likely influenced the structural biology of life, explaining the cysteine anomaly.
  • Lipophilic thiols function as a novel class of biological cytotoxins that selectively enhance oxidative damage in vivo.