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Related Concept Videos

Preparation and Reactions of Thiols02:33

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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Modification of secretory and transmembrane proteins entering the rough ER begins in the ER lumen. These modifications aid in protein folding and stabilize the acquired tertiary structure. Protein modifications in the rough ER co-occur at different stages of protein folding.
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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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Related Experiment Video

Updated: Feb 22, 2026

Combining Non-reducing SDS-PAGE Analysis and Chemical Crosslinking to Detect Multimeric Complexes Stabilized by Disulfide Linkages in Mammalian Cells in Culture
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Next-generation disulfide stapling: reduction and functional re-bridging all in one.

Maximillian T W Lee1, Antoine Maruani1, James R Baker1

  • 1Department of Chemistry , University College London , 20 Gordon Street , London , WC1H 0AJ , United Kingdom . Email: v.chudasama@ucl.ac.uk ; Tel: +44207 679 2077.

Chemical Science
|October 3, 2017
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Summary

A new disulfide stapling reagent enables reduction and re-bridging of disulfide bonds in peptides and proteins. This novel method achieves successful re-bridging, even in complex multi-disulfide systems, without unwanted scrambling.

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Area of Science:

  • Chemical Biology
  • Protein Chemistry
  • Bioconjugation Chemistry

Background:

  • Disulfide bonds are crucial for protein structure and function.
  • Current methods for disulfide manipulation can be limited or lead to scrambling.
  • Next-generation reagents are needed for precise control over disulfide chemistry.

Purpose of the Study:

  • To develop a novel reagent class for simultaneous disulfide reduction and functional re-bridging.
  • To demonstrate the efficacy of this new strategy across diverse peptide and protein systems.
  • To assess the reagent's performance in complex multi-disulfide environments.

Main Methods:

  • Design and synthesis of a novel disulfide stapling reagent.
  • Application of the reagent to various peptide and protein substrates.
  • Analysis of disulfide reduction and re-bridging efficiency.
  • Evaluation of disulfide scrambling in multi-disulfide systems.

Main Results:

  • A novel reagent class effectively mediates both disulfide reduction and functional re-bridging.
  • Successful application demonstrated across a range of peptides and proteins.
  • The strategy achieved functional re-bridging in a multi-disulfide system without scrambling.

Conclusions:

  • The developed reagent represents a significant advancement in disulfide stapling technology.
  • This method offers a robust tool for precise manipulation of disulfide bonds in biomolecules.
  • The reagent shows promise for applications requiring controlled disulfide engineering.