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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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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

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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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Peptide Bonds02:43

Peptide Bonds

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A peptide bond covalently attaches amino acids through a dehydration reaction. One amino acid's carboxyl group and another amino acid's amino group combine, releasing a water molecule. The resulting bond is the peptide bond. The products that such linkages form are peptides. As more amino acids join this growing chain, the resulting chain is a polypeptide. Each polypeptide has a free amino group at one end. This end has the N-terminal, or the amino-terminal, and the other end has a free...
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
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Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

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Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Bidirectional macrocyclization of peptides by double multicomponent reactions.

Manuel G Ricardo1, Fidel E Morales, Hilda Garay

  • 1Center for Natural Products Research, Faculty of Chemistry, University of Havana, Zapata y G, 10400, La Habana, Cuba. dgr@fq.uh.cu.

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This study introduces a novel bidirectional multicomponent reaction for synthesizing diverse N-alkylated macrocyclic peptides. This method efficiently expands chemical space for macrocyclic peptide discovery in chemical biology and drug development.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Chemical Biology

Background:

  • Macrocyclic peptides are valuable scaffolds in drug discovery, but their synthesis often requires diverse cyclization strategies.
  • Multicomponent reactions (MCRs) offer efficient routes to molecular complexity and diversity.
  • Expanding synthetic methodologies for macrocyclic peptides is crucial for accessing novel chemotypes.

Purpose of the Study:

  • To develop a novel bidirectional multicomponent approach for synthesizing N-alkylated macrocyclic peptides.
  • To explore the generation of diverse sequences and cross-linking positions within macrocyclic peptide structures.
  • To leverage MCRs for rapid scanning of macrocyclic peptide chemical space.

Main Methods:

  • Utilized a bidirectional multicomponent reaction strategy.
  • Employed two sequential Ugi reactions involving peptide diacids and diisocyanides.
  • Varied amino components and cyclization strategies to introduce diversity.

Main Results:

  • Successfully synthesized N-alkylated macrocyclic peptides with varied sequences and cross-linking positions.
  • Demonstrated the installation of exocyclic diversity by varying amino components.
  • Achieved skeletal diversity through different side chain and backbone cyclizations.

Conclusions:

  • The developed bidirectional multicomponent approach provides an efficient method for macrocyclic peptide synthesis.
  • This strategy enables rapid exploration of macrocyclic peptide chemical space.
  • The findings have significant implications for chemical biology and drug discovery applications.