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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.

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In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...

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Related Experiment Video

Updated: May 21, 2026

Resin-Assisted Capture Coupled with Isobaric Tandem Mass Tag Labeling for Multiplexed Quantification of Protein Thiol Oxidation

Resin-Assisted Capture Coupled with Isobaric Tandem Mass Tag Labeling for Multiplexed Quantification of Protein Thiol Oxidation

Published on: June 21, 2021

Oxidative stress, thiols, and redox profiles.

Craig Harris¹, Jason M Hansen

¹Toxicology Program, Department of Environmental Health Sciences, University of Michigan, Ann Arbor, MI, USA. charris@umich.edu

Methods in Molecular Biology (Clifton, N.J.)

|June 7, 2012

Summary

Oxidative stress in development is redefined by protein thiol modifications, not just glutathione levels. Accurate assessment requires measuring redox potential, reactive oxygen species, and protein thiol changes.

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Last Updated: May 21, 2026

Resin-Assisted Capture Coupled with Isobaric Tandem Mass Tag Labeling for Multiplexed Quantification of Protein Thiol Oxidation

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Profiling Thiol Redox Proteome Using Isotope Tagging Mass Spectrometry

Profiling Thiol Redox Proteome Using Isotope Tagging Mass Spectrometry

Published on: March 24, 2012

Area of Science:

Toxicology
Developmental Biology
Biochemistry

Background:

Oxidative stress contributes to developmental toxicity.
Traditional markers like glutathione (GSH)/glutathione disulfide (GSSG) may not fully capture cellular redox state.
Emerging understanding highlights reactive oxygen species (ROS) and thiol modifications in redox signaling.

Purpose of the Study:

To redefine oxidative stress based on protein thiol modifications.
To propose comprehensive methods for assessing redox status in developing organisms.
To link redox signaling nodes to developmental events.

Main Methods:

Quantitative assessment of intracellular redox potential and ROS production.
Measurement of soluble thiol oxidation.
Proteomic analysis of protein thiol oxidation states.

Main Results:

Redefinition of oxidative stress emphasizes posttranslational protein thiol modifications.
Thiol-based redox couples (e.g., GSH/GSSG, cysteine/cystine, thioredoxin) act as independent signaling nodes.
Proposed methods allow for accurate assessment of redox consequences in developing conceptuses.

Conclusions:

Accurate assessment of developmental toxicity requires a battery of redox measurements.
Protein thiol modifications are central to redox regulation and control.
Understanding these redox dynamics is crucial for developmental toxicology.