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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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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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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.
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Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
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  1. Home
  3. One-pot, Chemoselective Desulfurative Functionalization Of Cysteine Containing Peptides Using Pyridinium Salts
  1. Home
  3. One-pot, Chemoselective Desulfurative Functionalization Of Cysteine Containing Peptides Using Pyridinium Salts

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One-pot, chemoselective desulfurative functionalization of cysteine containing peptides using pyridinium salts

Jeroen W van den Heuvel1, Esther Olaniran Håkansson1, Bobo Skillinghaug1

  • 1Department of Medicinal Chemistry, Uppsala University, 751 23 Uppsala, Sweden. luke.odell@ilk.uu.se.

Chemical Communications (Cambridge, England)
|June 13, 2025

View abstract on PubMed

Summary
This summary is machine-generated.

Researchers developed a new method for modifying peptides using cysteine. This versatile strategy allows for diverse late-stage peptide functionalization, aiding in the discovery of novel pharmaceuticals.

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Area of Science:

  • Medicinal Chemistry
  • Organic Chemistry
  • Biochemistry

Background:

  • Peptide and protein modifications are crucial for pharmaceutical development.
  • Current cysteine-mediated peptide modification methods are limited, primarily to bioconjugation and disulfide bond formation.
  • Novel cysteine modification strategies are needed to expand pharmaceutical synthesis capabilities.

Purpose of the Study:

  • To develop a practical and versatile method for the late-stage functionalization of cysteine-containing peptides.
  • To explore new cysteine-mediated peptide modifications beyond traditional bioconjugation and disulfide formation.
  • To enable the synthesis of diverse peptide derivatives for pharmaceutical discovery.

Main Methods:

  • A three-step, one-pot desulfurative functionalization strategy was employed.
  • Pyridinium salts were utilized to facilitate the reaction.
  • A variety of nucleophiles, including amino acid side chains and pharmaceutical compounds, were used for peptide modification.

    • Main Results:

    • The method demonstrated diverse and selective functionalization of cysteine-containing peptides.
    • Successful application of the strategy for macrocyclization reactions was achieved.
    • The approach allows for efficient late-stage modification, expanding the scope of peptide derivatization.

    Conclusions:

    • The presented strategy offers a practical and versatile approach for cysteine-mediated peptide modification.
    • This method facilitates diverse late-stage derivatization, significantly aiding in the discovery and synthesis of new pharmaceuticals.
    • The findings open new avenues for peptide-based drug development.