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Related Concept Videos

Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Cycloaddition Reactions: Overview01:16

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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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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.
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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...
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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Rapid Arene Triazene Chemistry for Macrocyclization.

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We developed a fast peptide macrocyclization method using arene triazene chemistry. This creates stable cyclic peptides that release linear peptides upon UV or acid exposure, enabling new applications.

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Area of Science:

  • Organic Chemistry
  • Chemical Biology
  • Peptide Chemistry

Background:

  • Peptide macrocyclization is crucial for drug discovery and chemical biology.
  • Existing methods often require protecting groups or harsh conditions.
  • Developing rapid and versatile macrocyclization strategies is essential.

Purpose of the Study:

  • To introduce a novel, rapid arene triazene strategy for peptide macrocyclization.
  • To create cyclic peptides with a stimuli-responsive triazene linkage.
  • To demonstrate the method's applicability to diverse peptide structures and modifications.

Main Methods:

  • Utilizing rapid arene triazene chemistry for chemoselective cyclization of unprotected peptides.
  • Employing secondary amines and p-amino phenylalanine for triazene formation.
  • Investigating stimuli-responsive ring-opening under UV radiation and acidic conditions.

Main Results:

  • Successful synthesis of 18- to 66-membered monocycles and bicycles in one pot.
  • Demonstrated high stability of triazene cyclic peptides at neutral pH and harsh conditions.
  • Showcased stimuli-triggered release of intact linear peptides, followed by re-cyclization.

Conclusions:

  • The arene triazene strategy offers a rapid, efficient, and versatile approach to peptide macrocyclization.
  • The resulting cyclic peptides exhibit unique stimuli-responsive properties for controlled release.
  • This method holds promise for applications in drug delivery, chemical biology, and high-throughput screening.