Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

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.

Preparation and Reactions of Thiols

Preparation and Reactions of Thiols

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.

Structure and Nomenclature of Thiols and Sulfides

Structure and Nomenclature of Thiols and Sulfides

Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry, similar...

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.

Conversion of Alcohols to Alkyl Halides

Conversion of Alcohols to Alkyl Halides

This lesson delves into the conversion of alcohols to corresponding alkyl halides and the mechanism of action for different reagents. Typically, the hydroxyl group is first protonated to convert it to a stable leaving group. Consequently, based on the starting alcohol, the mechanism undergoes either of the nucleophilic substitution routes, SN1 or SN2. Tertiary alkyl halides are made using the two-step SN1 mechanism that occurs via a carbocation intermediate, which is stabilized by...

Acid Halides to Alcohols: Grignard Reaction

Acid Halides to Alcohols: Grignard Reaction

Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Gas-Phase Discrimination of Histidine Epimers in Peptides by Silver-Cation-Assisted Energy-Resolved Mass Spectrometry.

Journal of the American Society for Mass Spectrometry·2026

Same author

Proximity-Induced Transfer of a Mass Tag Enables Direct Profiling of Active Matrix Metalloproteases.

Angewandte Chemie (International ed. in English)·2026

Same author

<i>In Silico</i> and <i>in Vitro</i> Selection Method of Peptide Substrates for Protease Selectivity.

ACS biomaterials science & engineering·2025

Same author

Study of the impact of histidine configuration and position on analytical separation of tripeptides.

Journal of chromatography. A·2025

Same author

Silylated peptides as building blocks for material synthesis using sol-gel polymerization.

Faraday discussions·2025

Same author

Differentiation of Isomeric TAT1-CARNOSINE Peptides by Energy-Resolved Mass Spectrometry and Principal Component Analysis.

Molecules (Basel, Switzerland)·2025

Search research articles

Related Experiment Video

Updated: Jun 1, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

Oxyfold: a simple and efficient solid-supported reagent for disulfide bond formation.

Pascal Verdié¹, Luisa Ronga, Michèle Cristau

¹Institut des Biomolécules Max Mousseron IBMM, UMR CNRS 5247, 15 avenue Charles Flahault, 34000 Montpellier, France.

Chemistry, an Asian Journal

|June 10, 2011

Summary

This summary is machine-generated.

Novel polymer-supported reagents made from oxidized methionines simplify peptide disulfide bond formation. Their cost-effectiveness and easy preparation make them ideal for creating disulfide bridges in peptides.

More Related Videos

A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles

A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles

Published on: December 23, 2016

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

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

Published on: May 2, 2019

Related Experiment Videos

Last Updated: Jun 1, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles

A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles

Published on: December 23, 2016

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

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

Published on: May 2, 2019

Area of Science:

Polymer Chemistry
Organic Synthesis
Biochemistry

Background:

Disulfide bonds are crucial for peptide structure and function.
Existing methods for disulfide bond formation can be complex or costly.

Purpose of the Study:

To develop and describe novel polymer-supported reagents for efficient disulfide bond formation.
To present oxidized methionines grafted onto a solid support as a new class of reagents.

Main Methods:

Synthesis of polymer-supported oxidized methionines via N-carboxyanhydride polymerization on beads.
Application of these reagents for the formation of disulfide bridges in peptides.

Main Results:

Successful synthesis of a family of polymer-supported oxidized methionine reagents.
Demonstration of the reagents' efficacy in forming disulfide bonds.
Highlighting the cost-effectiveness and simplicity of reagent preparation.

Conclusions:

Polymer-supported oxidized methionines are effective and practical reagents for peptide disulfide bond formation.
The described method offers an advantageous alternative for synthesizing peptides with disulfide bridges.