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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.8K
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.
3.8K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

5.1K
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.
5.1K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

8.0K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
8.0K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.9K
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.
2.9K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

10.6K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
10.6K
Acid-Catalyzed Aldol Addition Reaction01:15

Acid-Catalyzed Aldol Addition Reaction

3.5K
The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
3.5K

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Efficient and Site-specific Antibody Labeling by Strain-promoted Azide-alkyne Cycloaddition
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Fluorogenic Strain-Promoted Alkyne-Diazo Cycloadditions.

Frédéric Friscourt1,2, Christoph J Fahrni3, Geert-Jan Boons4

  • 1Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602 (USA), Fax: (+1) 706-542-4412.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 3, 2015
PubMed
Summary

A novel fluorogenic probe, Fl-DIBO, enables highly sensitive detection of biomolecules. It reacts with diazo-tagged proteins, producing a significant fluorescence enhancement for clear visualization without probe washout.

Keywords:
bioorthogonalclick chemistrycycloadditioncyclooctynefluorogenic probes

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Area of Science:

  • Chemical Biology
  • Materials Science
  • Organic Chemistry

Background:

  • Fluorogenic reactions are valuable for detecting compounds in bioconjugation and materials science.
  • Developing new probes with enhanced fluorescence is crucial for sensitive molecular detection.

Purpose of the Study:

  • To develop and characterize a novel fluorogenic probe, Fl-DIBO, for bio-labeling applications.
  • To investigate the reaction kinetics and fluorescence properties of Fl-DIBO with various reaction partners.

Main Methods:

  • Synthesis of a dibenzocyclooctyne derivative with a cyclopropenone moiety (Fl-DIBO).
  • Strain-promoted cycloaddition reactions with azides, nitrones, nitrile oxides, and diazo-derivatives.
  • Quantum chemical calculations to understand fluorescence quenching mechanisms.
  • Application of Fl-DIBO for labeling diazo-tagged proteins.

Main Results:

  • Fl-DIBO reacts rapidly and catalyst-free with various dienophiles.
  • Reaction with monosubstituted diazo reagents yields 1H-pyrazoles with ~160-fold fluorescence enhancement and >10,000-fold brightness increase.
  • Quantum chemical calculations suggest low-lying (n,π*) states cause quenching in 3H-pyrazoles from disubstituted diazo compounds.
  • Successful labeling of diazo-tagged proteins with Fl-DIBO, showing no background signal and eliminating the need for probe washout.

Conclusions:

  • Fl-DIBO is a highly effective fluorogenic probe for bio-imaging applications.
  • The probe offers significant advantages for visualizing biomolecules labeled with diazo-derivatives.
  • This work advances the development of sensitive and efficient bio-labeling strategies.