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Related Concept Videos

Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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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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Olefin Metathesis Polymerization: Overview01:13

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Preparation and Reactions of Thiols02:33

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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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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
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Anionic Chain-Growth Polymerization: Overview01:20

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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Cysteine-functional polymers via thiol-ene conjugation.

Matthias Kuhlmann1, Oliver Reimann, Christian P R Hackenberger

  • 1Department for Functional Materials in Medicine and Dentistry, University of Würzburg, Pleicherwall 2, 97070, Würzburg, Germany.

Macromolecular Rapid Communications
|February 4, 2015
PubMed
Summary

A new thiofunctional thiazolidine enables cysteine residue introduction using thiol-ene reactions in polymer functionalization. This method allows precise control over cysteine content for advanced material synthesis.

Keywords:
chemoselectivityconjugated polymersfunctionalization of polymersprotecting groupsthiol-ene chemistry

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Bioconjugation Chemistry

Background:

  • Thiol-ene click chemistry is a versatile tool for polymer modification.
  • Introducing specific amino acid residues like cysteine into polymers enables advanced functionalities.
  • Existing methods for cysteine incorporation can be limited in scope or efficiency.

Purpose of the Study:

  • To develop a novel thiofunctional building block for efficient cysteine residue introduction into polymers.
  • To demonstrate the utility of this building block for polymer-analogue functionalization using thiol-ene reactions.
  • To establish a robust method for quantifying cysteine content in functionalized polymers.

Main Methods:

  • Synthesis of a novel thiofunctional thiazolidine reactant.
  • Functionalization of allyl-functional polyglycidol (PG) via thiol-ene coupling.
  • Redox-insensitive quantification of cysteine content using a modified trinitrobenzenesulfonic acid (TNBSA) assay.
  • Chemoselective peptide modification via native chemical ligation at cysteine-functionalized PG.

Main Results:

  • A three-step synthesis route for the thiofunctional thiazolidine was established.
  • Allyl-functional PG was successfully modified to incorporate cysteine residues.
  • The TNBSA assay provided accurate and redox-insensitive quantification of cysteine content.
  • Native chemical ligation demonstrated the utility of cysteine-functional PG for bioconjugation.

Conclusions:

  • The developed thiofunctional thiazolidine is a valuable building block for introducing cysteine residues via thiol-ene chemistry.
  • This approach offers a generic and straightforward method for creating cysteine-functional materials.
  • The combination of synthesis, coupling, and quantification broadens the scope of thiol-ene chemistry for material science.