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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.8K
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.
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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

2.4K
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.
2.4K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.7K
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.
3.7K
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

3.4K
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.
3.4K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

3.1K
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.
3.1K
Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives01:35

Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

2.8K
Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.
2.8K

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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

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Decarboxylative Peptide Macrocyclization through Photoredox Catalysis.

Stefan J McCarver1, Jennifer X Qiao2, Joseph Carpenter2

  • 1Merck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ, 08544, USA.

Angewandte Chemie (International Ed. in English)
|November 19, 2016
PubMed
Summary
This summary is machine-generated.

A new photoredox method efficiently synthesizes cyclic peptides, including those with gamma-amino acids. This versatile technique works with various amino acids and is useful for creating complex molecules like the somatostatin analogue COR-005.

Keywords:
Michael additiondecarboxylationmacrocyclespeptidesphotoredox catalysis

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Development of a Backbone Cyclic Peptide Library as Potential Antiparasitic Therapeutics Using Microwave Irradiation
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Development of a Backbone Cyclic Peptide Library as Potential Antiparasitic Therapeutics Using Microwave Irradiation
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Area of Science:

  • Organic Chemistry
  • Peptide Synthesis
  • Photoredox Catalysis

Background:

  • Cyclic peptides are important in drug discovery.
  • Efficient synthesis of cyclic peptides, especially those containing gamma-amino acids, remains a challenge.
  • Existing methods may lack tolerance for diverse amino acid functionalities.

Purpose of the Study:

  • To develop a novel method for the decarboxylative macrocyclization of peptides.
  • To enable the efficient synthesis of cyclic peptides containing gamma-amino acids.
  • To demonstrate the utility of the method for synthesizing bioactive molecules.

Main Methods:

  • Developed a photoredox-catalyzed decarboxylative macrocyclization reaction.
  • Utilized peptides with N-terminal Michael acceptors as linear precursors.
  • Applied the method to linear precursors of varying lengths (3-15 amino acids).

Main Results:

  • Achieved efficient cyclization of linear peptide precursors.
  • The method is tolerant of various natural and non-proteinogenic amino acid functionalities.
  • Successfully synthesized COR-005, a somatostatin analogue in clinical trials, showcasing preparative utility.

Conclusions:

  • The developed photoredox method provides an efficient route to cyclic peptides containing gamma-amino acids.
  • This synthetic strategy is versatile and applicable to complex peptide structures.
  • The method holds promise for the synthesis of peptide-based therapeutics.