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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 of Alkynes: Alkylation Reaction

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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...

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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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...

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Updated: Nov 1, 2025

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Published on: September 28, 2022

Cleavable and tunable cysteine-specific arylation modification with aryl thioethers.

Jian Li¹, Jun-Jie Deng¹, Zhibin Yin¹

¹Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University Guangzhou 510006 P. R. China xiongxf7@mail.sysu.edu.cn.

Chemical Science

|June 25, 2021

Summary

Researchers developed a new method for modifying cysteine in peptides and proteins using aryl thioethers. This tunable approach allows for efficient bioconjugation and controlled regeneration of native peptides.

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Published on: August 1, 2018

Area of Science:

Bioconjugation Chemistry
Organic Synthesis
Chemical Biology

Background:

Cysteine's nucleophilic thiol group makes it a prime target for peptide and protein modification.
Existing modification methods may lack selectivity, efficiency, or tunability.

Purpose of the Study:

To develop a cleavable and tunable covalent modification strategy for cysteine-containing peptides and proteins.
To introduce novel aryl thioether reagents for selective bioconjugation.

Main Methods:

Synthesis of novel aryl thioethers with varying steric and electronic properties.
Application of the S_NAr reaction for cysteine modification under mild, biocompatible conditions.
Characterization of modified peptides/proteins and assessment of regeneration capabilities.

Main Results:

Highly efficient and selective bioconjugation of cysteine residues was achieved.
A variety of functional groups, including affinity and fluorescent tags, were tolerated.
Tunable regeneration of native peptides was demonstrated by adjusting aryl thioether structure.

Conclusions:

The developed S_NAr approach provides a versatile and controllable method for cysteine modification.
This strategy enables the introduction of diverse functionalities onto peptides and proteins.
The tunable cleavage allows for potential applications in controlled release or dynamic labeling.