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Related Concept Videos

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

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

12.1K
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.
12.1K
The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry07:02

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry

14.2K
A simple two-step approach involving rubber modification and cross-linking yields fully reworkable, elastic rubber products.
14.2K
Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors01:31

Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors

5.8K
The Diels–Alder reaction is thermally reversible, meaning that the reaction reverts to the starting diene and dienophile under suitable temperatures. The forward reaction gives a cyclohexene derivative and is favored at low to medium temperatures. The reverse process, also called retro-Diels–Alder reaction, is a ring-opening process favored at high temperatures.
5.8K
Harnessing the Bioorthogonal Inverse Electron Demand Diels-Alder Cycloaddition for Pretargeted PET Imaging10:47

Harnessing the Bioorthogonal Inverse Electron Demand Diels-Alder Cycloaddition for Pretargeted PET Imaging

9.2K
The bioorthogonal inverse electron demand Diels-Alder cycloaddition has been harnessed to create an effective and modular pretargeted PET imaging strategy for cancer. In this protocol, the steps of this methodology are described in the context of a model system employing the colorectal cancer targeted antibody huA33 and a 64Cu-labeled radioligand.
9.2K
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

5.1K
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
5.1K
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

7.2K
In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction. 
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
7.2K

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Related Experiment Video

Updated: Jan 19, 2026

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
07:02

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry

Published on: August 25, 2016

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Versatile Peptide Macrocyclization with Diels-Alder Cycloadditions.

Jeffrey E Montgomery, Justin A Donnelly, Sean W Fanning

    Journal of the American Chemical Society
    |September 17, 2019
    PubMed
    Summary
    This summary is machine-generated.

    Diels-Alder cyclization offers a versatile method to stabilize peptides, enhancing their drug-like properties. This approach improves protease resistance and biological activity for therapeutic applications.

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    [4+2] Cycloaddition of Conjugated Dienes: Diels&amp;#8211;Alder Reaction
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    Diels&amp;#8211;Alder vs Retro-Diels&amp;#8211;Alder Reaction: Thermodynamic Factors
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    [4+2] Cycloaddition of Conjugated Dienes: Diels&amp;#8211;Alder Reaction
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    Diels&amp;#8211;Alder vs Retro-Diels&amp;#8211;Alder Reaction: Thermodynamic Factors
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    Area of Science:

    • Medicinal Chemistry
    • Organic Chemistry
    • Biochemistry

    Background:

    • Macrocyclization enhances peptide drug properties by preorganizing molecular structure.
    • Existing methods for peptide stabilization have limitations in scope and application.

    Purpose of the Study:

    • To explore Diels-Alder [4 + 2] cycloadditions as a novel strategy for peptide macrocyclization and stabilization.
    • To assess the impact of Diels-Alder cyclization on peptide structural rigidity, protease resistance, and biological activity.

    Main Methods:

    • Diels-Alder reactions were performed on various peptide scaffolds in solid-phase and aqueous conditions.
    • NMR spectroscopy and molecular dynamics simulations were used to analyze peptide structure and stereochemistry.
    • Cocrystallography was employed to determine the structure of stabilized peptides bound to their targets.

    Main Results:

    • Diels-Alder cyclization proceeded rapidly and in high yield, forming stable peptide structures.
    • The reaction demonstrated tunable stereochemical control, favoring the endo adduct.
    • Diels-Alder cyclized peptides exhibited increased protease resistance and enhanced biological activity.
    • Structural analysis confirmed the endo stereochemistry and its contribution to target binding.

    Conclusions:

    • Diels-Alder cyclization is a versatile and effective method for stabilizing diverse peptide structural motifs.
    • This chemistry enhances peptide pharmacologic properties, offering a promising avenue for drug development.
    • The unique architecture of Diels-Alder adducts can directly contribute to target binding interactions.