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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.

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.

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,...

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Updated: Jul 6, 2025

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

Published on: March 6, 2019

Silicon-Containing Thiol-Specific Bioconjugating Reagent.

Zhenguo Zhang^1,2, Lanyang Li³, Hailun Xu³

¹College of Advanced Interdisciplinary Science and Technology, Henan University of Technology, Zhengzhou 450001, China.

Journal of the American Chemical Society

|January 10, 2024

Summary

A novel silicon-based bioconjugation reagent offers enhanced selectivity for thiol reactions. This advancement improves protein conjugation and antibody-drug conjugate synthesis, opening new possibilities in medicinal chemistry.

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Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

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Published on: March 6, 2019

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Synthesis of Protein Bioconjugates via Cysteine-maleimide Chemistry

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Published on: July 20, 2016

Area of Science:

Chemical Biology
Medicinal Chemistry
Materials Science

Background:

Traditional bioconjugation reagents often lack selectivity and can be prone to retro-reactions.
Developing new reagents with improved properties is crucial for advancing protein modification and drug delivery systems.

Purpose of the Study:

To develop a novel silicon-containing bioconjugation reagent for selective thiol modification.
To evaluate the reagent's performance in terms of chemoselectivity, yield, and compatibility with biomolecules.

Main Methods:

Synthesis of a new silicon-containing bioconjugation reagent.
Testing the reagent's reactivity with various thiols and unsaturated carbonyl compounds.
Assessing the stability and biocompatibility of the resulting conjugates.

Main Results:

The silicon reagent demonstrated high chemoselectivity for thiols, surpassing traditional reagents.
Reactions proceeded with moderate to high yields under biocompatible conditions.
Resulting conjugates showed good stability with biomolecules, suitable for antibody-drug conjugate synthesis.

Conclusions:

The new silicon-based reagent offers a versatile and effective tool for thiol-specific bioconjugation.
Its properties enable applications in protein modification, antibody-drug conjugate synthesis, and inorganic-organic hybrid materials.
This work expands the toolkit for bioanalytical science and medicinal chemistry researchers.