Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

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

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

11.9K
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.
11.9K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

4.5K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
4.5K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.2K
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.
3.2K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

5.2K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
5.2K
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

7.0K
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...
7.0K
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

4.9K
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,...
4.9K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Toward a Comparable Reactivity Framework for Type I Photoinitiators in Photocleavage, Photopolymerization and Light-Driven Additive Manufacturing.

Journal of the American Chemical Society·2026
Same author

Macromolecules with Tunable Fluorescence via Photochemical Step-Growth Polymerization.

ACS macro letters·2026
Same author

Impact of BHT Additive on the Optical and Reactive Behavior of Fluorescent Peroxynitrite Probes.

ACS omega·2026
Same author

Understanding Wavelength-Dependent Photopolymerizations via Nano-Second Resolved Transient Spectroscopy.

Journal of the American Chemical Society·2026
Same author

Urinary detection of therapy-induced senescence and fibrosis using an injectable albumin-based nanoprobe.

Nature aging·2026
Same author

Microglia encapsulation in nanozyme-loaded hydrogels: response to oxidative stress and inflammation.

Nanomedicine (London, England)·2026

Related Experiment Video

Updated: Dec 13, 2025

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

14.1K

Hetero-Diels-Alder Cycloaddition with RAFT Polymers as Bioconjugation Platform.

Ana Beloqui1,2,3,4, Shivshankar R Mane1,2, Marcel Langer2

  • 1Institute of Biological and Chemical Systems (IBCS), Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany.

Angewandte Chemie (International Ed. in English)
|July 31, 2020
PubMed
Summary

We developed a new method for attaching polymers to proteins using a specific chemical reaction. This process creates smart materials that respond to temperature changes, controlled entirely by the polymer chains.

Keywords:
Diels-Alder cycloadditionbioconjugationend grouppolymerprotein

More Related Videos

Harnessing the Bioorthogonal Inverse Electron Demand Diels-Alder Cycloaddition for Pretargeted PET Imaging
10:47

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

Published on: February 3, 2015

9.1K
Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

7.2K

Related Experiment Videos

Last Updated: Dec 13, 2025

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

14.1K
Harnessing the Bioorthogonal Inverse Electron Demand Diels-Alder Cycloaddition for Pretargeted PET Imaging
10:47

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

Published on: February 3, 2015

9.1K
Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

7.2K

Area of Science:

  • Polymer Chemistry
  • Bioconjugation Chemistry
  • Materials Science

Background:

  • Reversible-addition fragmentation chain-transfer (RAFT) polymerization is a versatile method for synthesizing polymers.
  • Bioconjugation is essential for creating functional materials with biological applications.
  • Developing efficient and mild conjugation methods is crucial for preserving protein activity.

Purpose of the Study:

  • To introduce a novel bioconjugation strategy for RAFT-polymerized polymers.
  • To achieve efficient and catalyst-free conjugation under mild conditions.
  • To create thermoresponsive bioconjugates with polymer-controlled aggregation.

Main Methods:

  • Synthesis of polymers with a terminal thiocarbonylthio moiety via RAFT polymerization.
  • Hetero-Diels-Alder cycloaddition reaction between the polymer's terminal group and a diene-modified protein.
  • Characterization of the resulting bioconjugates.

Main Results:

  • Quantitative bioconjugation achieved within hours at ambient temperature and neutral pH.
  • The method requires no catalyst, simplifying the process.
  • The resulting bioconjugates exhibit thermoresponsive behavior, with aggregation controlled by the polymer chains.

Conclusions:

  • The developed hetero-Diels-Alder cycloaddition provides an efficient and mild platform for polymer-protein bioconjugation.
  • This method enables the creation of advanced thermoresponsive materials for various applications.
  • The inherent terminal group of RAFT polymers can be effectively utilized for bioconjugation.