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Related Concept Videos

Radical Autoxidation01:20

Radical Autoxidation

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...
Electron Transport Chain: Complex III and IV01:43

Electron Transport Chain: Complex III and IV

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...
Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
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Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions generating free carboxylic acid...
Oxidation of Alcohols02:37

Oxidation of Alcohols

In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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: Jun 24, 2026

Resin-Assisted Capture Coupled with Isobaric Tandem Mass Tag Labeling for Multiplexed Quantification of Protein Thiol Oxidation
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Cysteine oxidation by the superoxide radical: a theoretical study.

Bruno Cardey1, Mironel Enescu

  • 1Laboratoire de Chimie Physique et Rayonnements UMR CEA, University of Franche-Comte, E4, 16 route de Gray, 25030 Besançon Cedex, France.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|April 1, 2009
PubMed
Summary

Superoxide radical oxidation of cysteine residues is influenced by molecular environment. Hydrogen bonding and electrostatics alter reaction barriers, with sulfinyl radical formation dominating in aqueous solution and thiyl radical formation in hydrophobic settings.

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Published on: May 2, 2019

Area of Science:

  • Biochemistry
  • Computational Chemistry
  • Chemical Physics

Background:

  • Cysteine oxidation is crucial in biological processes.
  • Superoxide radical is a key reactive oxygen species.
  • Understanding cysteine oxidation mechanisms is vital.

Purpose of the Study:

  • To investigate cysteine residue oxidation by superoxide radical.
  • To elucidate the role of molecular environment on oxidation pathways.
  • To compare gas phase and aqueous solution reaction dynamics.

Main Methods:

  • Utilized the integrated molecular orbital+molecular orbital (IMOMO) method.
  • Combined quadratic configuration interaction [QCISD(T)] and density functional (DFT) methods.
  • Systematically varied attack directions and cysteine conformations.

Main Results:

  • Hydrogen bonding and electrostatic interactions significantly impact reaction energy barriers.
  • Sulfinyl radical formation is the dominant oxidation channel in aqueous solution.
  • Thiyl radical formation becomes dominant in highly hydrophobic environments.

Conclusions:

  • The molecular environment dictates the primary cysteine oxidation pathway by superoxide.
  • Computational methods provide insights into reactive oxygen species interactions with amino acids.
  • Reaction mechanisms are sensitive to local environmental factors like polarity.