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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.2K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
3.2K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.0K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.0K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

1.9K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
1.9K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

1.9K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
1.9K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

3.3K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
3.3K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

1.9K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
1.9K

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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
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Amine-selective bioconjugation using arene diazonium salts.

Stefan Diethelm1, Michael A Schafroth, Erick M Carreira

  • 1Laboratorium für Organische Chemie, ETH Zürich , HCI H335, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland.

Organic Letters
|July 15, 2014
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Summary

A new bioconjugation method uses diazonium terephthalates to efficiently and irreversibly link complex molecules to proteins under mild conditions. This strategy enables direct coupling of natural products to proteins with high fidelity.

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Area of Science:

  • Chemical Biology
  • Bioconjugation Chemistry
  • Protein Modification

Background:

  • Bioconjugation is crucial for developing diagnostics, therapeutics, and research tools.
  • Existing methods often face challenges with efficiency, reversibility, or harsh reaction conditions.
  • There is a need for robust and versatile bioconjugation strategies.

Purpose of the Study:

  • To develop a novel, efficient, and irreversible bioconjugation strategy.
  • To enable the direct coupling of complex natural products to proteins.
  • To establish a method that proceeds under mild conditions with short reaction times.

Main Methods:

  • Utilizing a novel coupling reaction between diazonium terephthalates and protein amines.
  • Employing a vicinal ester-mediated cyclization for irreversible linkage.
  • Optimizing reaction conditions for efficiency and speed.

Main Results:

  • Demonstrated a highly efficient and irreversible bioconjugation reaction.
  • Successfully coupled densely functionalized, complex natural products to proteins.
  • Achieved conjugation under mild conditions with short reaction times and low reactant concentrations.

Conclusions:

  • The diazonium terephthalate strategy offers a powerful new tool for protein modification.
  • This method provides a robust platform for creating novel protein-based conjugates.
  • The approach is suitable for complex molecules and diverse biological applications.