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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

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.
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

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, the...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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.
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

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 on...
Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors01:31

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

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

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

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

Published on: August 25, 2016

A "diels-alderase" at last.

Craig A Townsend1

  • 1Department of Chemistry, The Johns Hopkins University, 3400 N. Charles Street, Baltimore, MD 21218, USA. ctownsend@jhu.edu

Chembiochem : a European Journal of Chemical Biology
|July 29, 2011
PubMed
Summary
This summary is machine-generated.

Enzymes rarely catalyze electrocyclization reactions. A newly characterized Diels-Alderase enzyme, however, accelerates a [4+2] cycloaddition reaction by 500-fold, offering insights into metabolic pathway limitations.

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Area of Science:

  • Biochemistry
  • Enzymology
  • Metabolic Pathways

Background:

  • Electrocyclization reactions are uncommon in biological systems.
  • The Diels-Alder reaction is a type of [4+2] cycloaddition.
  • Understanding enzymatic catalysis is crucial for metabolic engineering.

Purpose of the Study:

  • To investigate the catalytic mechanism of a newly characterized Diels-Alderase.
  • To quantify the rate enhancement provided by the enzyme for a [4+2] cycloaddition.
  • To explore the implications of enzymatic Diels-Alder reactions in metabolic pathways.

Main Methods:

  • Characterization of a monofunctional Diels-Alderase enzyme.
  • Enzymatic assays to measure reaction rates.
  • Comparison of enzymatic and non-enzymatic reaction speeds.

Main Results:

  • A Diels-Alderase enzyme was successfully identified and characterized.
  • The enzyme demonstrated a significant 500-fold rate enhancement for the catalyzed [4+2] cycloaddition.
  • This represents a rare example of enzymatic Diels-Alder catalysis in a metabolic context.

Conclusions:

  • Enzymatic catalysis can overcome the rarity of Diels-Alder reactions in metabolism.
  • The characterized Diels-Alderase provides a model for understanding enzyme-mediated cycloadditions.
  • Further research may uncover more such enzymes and their metabolic roles.