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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

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 generated carbocation,...
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic rearrangements are...
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

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Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Radical Chain-Growth Polymerization: Overview01:10

Radical Chain-Growth Polymerization: Overview

Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...

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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Side chain-to-side chain cyclization by click reaction.

Alexandra Le Chevalier Isaad1, Anna Maria Papini, Michael Chorev

  • 1Laboratory of Peptide & Protein Chemistry & Biology, Polo Scientifico e Tecnologico, University of Florence, I-50019 Sesto Fiorentino, Italy.

Journal of Peptide Science : an Official Publication of the European Peptide Society
|May 21, 2009
PubMed
Summary
This summary is machine-generated.

This study details a protocol for synthesizing heterodetic cyclopeptides using copper(I)-catalyzed azide-alkyne Huisgen cycloaddition (CuAAC). This click chemistry method creates novel triazolyl-containing peptide structures for potential therapeutic applications.

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Area of Science:

  • Chemical Biology
  • Organic Chemistry
  • Peptide Science

Background:

  • Copper(I)-catalyzed azide-alkyne 1,3-dipolar Huisgen cycloaddition (CuAAC) is a highly efficient click reaction.
  • CuAAC has significant applications in peptide and protein sciences.
  • Intramolecular side chain-to-side chain CuAAC for creating novel cyclopeptides is of particular interest.

Purpose of the Study:

  • To provide a detailed protocol for synthesizing heterodetic cyclopeptides.
  • To demonstrate a prototypical intramolecular CuAAC reaction.
  • To utilize a peptide sequence derived from parathyroid hormone-related protein as a model system.

Main Methods:

  • Copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC).
  • Intramolecular side chain-to-side chain reaction.
  • Synthesis of model heterodetic cyclopeptides.

Main Results:

  • A detailed protocol for synthesizing model heterodetic cyclopeptides was established.
  • The study successfully demonstrated an intramolecular CuAAC reaction.
  • A 1,4-disubstituted [1,2,3]triazolyl-containing bridge was formed within the cyclopeptide structure.

Conclusions:

  • The developed protocol enables the synthesis of novel heterodetic cyclopeptides.
  • Intramolecular CuAAC is a viable method for constructing complex peptide architectures.
  • This approach offers a pathway for creating new peptide-based therapeutics.