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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.

Protection of Alcohols

Protection of Alcohols

This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...

Protecting Groups for Aldehydes and Ketones: Introduction

Protecting Groups for Aldehydes and Ketones: Introduction

Protecting groups are compounds that can bind to a specific functional group in the presence of other functional groups to protect them from undesired chemical reactions. These compounds can selectively bind to particular functional groups and advance chemoselective reactions in polyfunctional systems (Figure 1). After the functional group has served its purpose, it is removed by reacting it with specific compounds.

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...

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.

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Updated: Jun 19, 2026

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

Published on: October 15, 2019

Wavelength-selective photoactivatable protecting groups for thiols.

Nico Kotzur¹, Benoît Briand, Michael Beyermann

¹Leibniz-Institut für Molekulare Pharmakologie, 13125 Berlin, Germany.

Journal of the American Chemical Society

|October 30, 2009

Summary

This summary is machine-generated.

Researchers developed water-soluble photolabile protecting groups for thiols. These groups enable wavelength-selective photocleavage of cysteine derivatives and peptides using light.

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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

Area of Science:

Organic Chemistry
Photochemistry
Biochemistry

Background:

Photolabile protecting groups are crucial for selective chemical modifications.
Existing protecting groups for thiols often lack water solubility or wavelength tunability.

Purpose of the Study:

To develop and characterize novel, water-soluble photolabile protecting groups for thiols.
To demonstrate wavelength-selective photocleavage of differentially protected cysteine residues.
To validate the concept in a model peptide system.

Main Methods:

Synthesis and characterization of new 2-nitrobenzyl and (coumarin-4-yl)methyl-based photolabile protecting groups.
Spectroscopic analysis to determine absorption maxima and photocleavage efficiencies.
Selective photocleavage experiments on binary mixtures of S-protected cysteine derivatives and peptide conjugates.

Main Results:

Efficient and water-soluble photolabile protecting groups were successfully developed.
Two new protecting groups were synthesized and characterized.
Wavelength-selective photocleavage of binary mixtures of protected cysteine derivatives was achieved using different wavelengths (> or = 402 nm, > or = 436 nm, and > or = 325 nm).
The method was successfully applied to selectively cleave S-protected cysteine residues in resact peptide derivatives.

Conclusions:

Novel photolabile protecting groups offer efficient and water-soluble thiol protection.
Differential wavelength-selective photocleavage enables precise control over peptide modification.
This strategy is applicable to complex biomolecules, facilitating advanced biochemical research.