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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

7.3K
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.
7.3K
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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Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

11.9K
Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
11.9K
Carboxylic Acids to Primary Alcohols: Hydride Reduction01:17

Carboxylic Acids to Primary Alcohols: Hydride Reduction

4.5K
Carboxylic acids, upon reaction with strong reducing agents such as lithium aluminum hydride followed by hydrolysis, undergo reduction to form primary alcohols.
4.5K
Acid Halides to Alcohols: LiAlH4 Reduction01:19

Acid Halides to Alcohols: LiAlH4 Reduction

3.7K
Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
3.7K
Redox Reactions01:24

Redox Reactions

58.0K
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...
58.0K

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Updated: Dec 25, 2025

Combining Non-reducing SDS-PAGE Analysis and Chemical Crosslinking to Detect Multimeric Complexes Stabilized by Disulfide Linkages in Mammalian Cells in Culture
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Combining Non-reducing SDS-PAGE Analysis and Chemical Crosslinking to Detect Multimeric Complexes Stabilized by Disulfide Linkages in Mammalian Cells in Culture

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Breaking a Couple: Disulfide Reducing Agents.

Sinenhlanhla N Mthembu1,2, Anamika Sharma1,2, Fernando Albericio1,3,4

  • 1Peptide Science Laboratory, School of Chemistry and Physics, University of KwaZulu-Natal, Durban, 4001, South Africa.

Chembiochem : a European Journal of Chemical Biology
|March 21, 2020
PubMed
Summary
This summary is machine-generated.

This review covers methods for reducing disulfide bonds in cysteine-containing molecules. It emphasizes selecting appropriate reducing agents based on substrate solubility for chemistry and biochemistry applications.

Keywords:
Cysteinecystinedisulfide bridgesreducing agentssolid-phase peptide synthesis

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Area of Science:

  • Biochemistry
  • Organic Chemistry

Background:

  • Cysteine (Cys) is a key amino acid found in numerous natural and synthetic molecules.
  • The thiol group of cysteine often forms disulfide bonds, either intramolecularly or with other thiols.

Purpose of the Study:

  • To review various methods for the efficient reduction of disulfide bonds.
  • To guide the selection of appropriate reducing reagents based on substrate solubility.

Main Methods:

  • Literature review of disulfide bond reduction techniques.
  • Analysis of reducing agents and their compatibility with different substrate solubilities.

Main Results:

  • Disulfide bond reduction is crucial for many applications of cysteine-containing molecules.
  • Solubility is a key factor in choosing an effective reducing agent.

Conclusions:

  • Effective reduction of disulfide bonds is essential in chemistry and biochemistry.
  • Consideration of substrate solubility aids in selecting optimal reducing methods for cysteine derivatives.