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Related Concept Videos

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

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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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: 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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Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

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Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

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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.
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Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

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Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
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TPDYs: strained macrocyclic diynes for bioconjugation processes.

Bernard D'Onofrio1, Corentin Cruché1, Kirsten N Hurdal2

  • 1Department of Chemistry and Centre for Green Chemistry and Catalysis, Université de Montréal, 1375 Avenue Thérèse-Lavoie-Roux, Montréal, QC, H2V 0B3, Canada. shawn.collins@umontreal.ca.

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Summary
This summary is machine-generated.

A novel terphenyl diyne (TPDY) macrocycle enables efficient bioconjugation and SPAAC reactions. This unique molecule offers new possibilities for chemical biology and drug development.

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Area of Science:

  • Organic Chemistry
  • Chemical Biology
  • Macromolecular Chemistry

Background:

  • Strain-promoted azide-alkyne cycloaddition (SPAAC) is a key click chemistry reaction for bioconjugation.
  • Development of novel cyclooctyne alternatives with unique reactivity and stability is ongoing.
  • Macrocyclic scaffolds offer distinct structural and electronic properties compared to linear or small-ring systems.

Purpose of the Study:

  • To synthesize and characterize a novel terphenyl diyne (TPDY) macrocycle.
  • To evaluate the reactivity of the TPDY macrocycle in SPAAC and other cycloaddition reactions.
  • To demonstrate the utility of TPDY for protein bioconjugation.

Main Methods:

  • Synthesis of the 3,5-terphenyl diyne (TPDY) macrocycle.
  • Investigation of SPAAC reactions with azides yielding atropisomeric triazoles.
  • Exploration of cycloadditions with diazoacetates and tetrazines.
  • Bioconjugation of TPDY to proteins using microbial transglutaminase.

Main Results:

  • Successful synthesis of the bent 1,3-diyne containing TPDY macrocycle.
  • TPDY demonstrated activity in SPAAC, forming atropisomeric triazole products.
  • TPDY underwent cycloadditions with diazoacetates and tetrazines.
  • Efficient bioconjugation of TPDY to two proteins was achieved via a microbial transglutaminase-catalyzed reaction.
  • Stabilization of the TPDY diyne occurs through π and π* orbital interactions, unlike typical SPAAC reagents.

Conclusions:

  • The developed TPDY macrocycle is a versatile building block for click chemistry.
  • TPDY facilitates atropisomeric triazole formation and protein bioconjugation.
  • The unique electronic stabilization of the diyne in TPDY expands the scope of SPAAC reagents.