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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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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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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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Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

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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.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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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 Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Facile Peptide Macrocyclization and Multifunctionalization via Cyclen Installation.

Tsz-Lam Cheung1, Leo K B Tam2, Wing-Sze Tam1

  • 1Department of Chemistry, Hong Kong Baptist University, 224 Waterloo Road, Kowloon Tong, Kowloon, Hong Kong, China.

Small Methods
|April 9, 2024
PubMed
Summary
This summary is machine-generated.

This study introduces an efficient method for creating cyclen-peptide bioconjugates. The new strategy simplifies the synthesis of lanthanide probes for imaging applications.

Keywords:
cyclen‐peptide conjugateslanthanidesluminescencesolid phase peptide synthesisαvβ3 integrin

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Area of Science:

  • Bioconjugation Chemistry
  • Peptide Synthesis
  • Lanthanide Probes

Background:

  • Traditional cyclen-peptide bioconjugate synthesis is multi-step and complex.
  • Individual preparation and purification of cyclic peptides and cyclen derivatives are required.
  • A need exists for more efficient and versatile methods.

Purpose of the Study:

  • To develop an efficient strategy for peptide cyclization and functionalization.
  • To enable the creation of multifunctional cyclen-embedded cyclopeptides.
  • To demonstrate the utility of this method for lanthanide probe development.

Main Methods:

  • Three-component intermolecular crosslinking on solid-phase peptide synthesis.
  • Incorporation of cyclen derivatives into cyclic peptides.
  • Functionalization with lanthanide ions (Eu3+ and Gd3+).

Main Results:

  • High conversion yield achieved in the synthesis process.
  • Demonstrated successful preparation of cyclen-embedded cyclic arginylglycylaspartic acid (RGD) peptide.
  • Developed a luminescent Eu3+ complex for optical imaging and a Gd3+-based agent for MRI.

Conclusions:

  • The novel strategy offers an efficient route to cyclen-peptide bioconjugates.
  • This method allows for the creation of multifunctional probes with tunable properties.
  • The developed probes show promise for both in vitro and in vivo imaging applications.