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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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.
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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.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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Preparation of 1° Amines: Azide Synthesis01:22

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
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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.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Diversity-Oriented Peptide Stapling: A Third Generation Copper-Catalysed Azide-Alkyne Cycloaddition Stapling and

Phuong Thu Tran1, Christian Ørnbøl Larsen1, Tobias Røndbjerg1

  • 1Department of Drug Design and Pharmacology, University of Copenhagen, Universitetsparken 2, 2100, Copenhagen, Denmark.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 21, 2017
PubMed
Summary

This study introduces a new diversity-oriented peptide stapling method using copper-catalysed azide-alkyne cycloaddition. This approach enables easy diversification and radiolabelling of stapled peptides for medicinal chemistry applications.

Keywords:
CuAACbioconjugate chemistrypeptide chemistrypeptidomimeticsradiolabelling

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Area of Science:

  • Medicinal Chemistry
  • Organic Chemistry
  • Biochemistry

Background:

  • Macrocyclic constraints (peptide stapling) stabilize peptide conformations.
  • Copper-catalysed azide-alkyne cycloaddition (CuAAC) is a key peptide stapling technique.
  • Existing CuAAC methods lack facile diversification strategies.

Purpose of the Study:

  • To develop a diversity-oriented peptide stapling (DOPS) methodology.
  • To enable further conjugation and dimerization of stapled peptides.
  • To provide simple access to radiolabelled stapled peptides.

Main Methods:

  • Utilizing CuAAC chemistry for peptide stapling.
  • Incorporating two azide-modified amino acids into peptides.
  • Reacting peptides with 1,3,5-triethynylbenzene.

Main Results:

  • Efficient formation of (i, i+7)- and (i, i+9)-stapled peptides.
  • Introduction of a single free alkyne on the staple for further modification.
  • Facile access to radiolabelled stapled peptides via catalytic tritiation.

Conclusions:

  • The DOPS methodology offers a versatile platform for peptide modification.
  • This method enhances the utility of CuAAC in peptide drug discovery.
  • The ability to easily radiolabel stapled peptides is significant for diagnostics and therapeutics.