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Related Concept Videos

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’

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Related Experiment Video

Updated: Jun 14, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
11:09

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Published on: August 1, 2018

On-resin peptide macrocyclization using thiol-ene click chemistry.

Alex A Aimetti1, Richard K Shoemaker, Chien-Chi Lin

  • 1Department of Chemical & Biological Engineering, University of Colorado, Boulder, CO 80309, USA.

Chemical Communications (Cambridge, England)
|April 10, 2010
PubMed
Summary

A new method enables rapid on-resin peptide cyclization using thiol-ene photochemistry. This strategy efficiently incorporates diverse alkenes via cysteine residues, offering a versatile synthetic tool.

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Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides

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Last Updated: Jun 14, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Published on: August 1, 2018

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Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides
09:54

Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides

Published on: August 20, 2018

Area of Science:

  • Organic Chemistry
  • Biochemistry
  • Photochemistry

Background:

  • Peptide synthesis is crucial for drug discovery and development.
  • Current methods for peptide cyclization can be complex and time-consuming.
  • There is a need for efficient and versatile cyclization strategies.

Purpose of the Study:

  • To develop a rapid and versatile synthetic strategy for on-resin peptide cyclization.
  • To utilize thiol-ene photochemistry for efficient peptide backbone modification.
  • To enable orthogonal incorporation of alkenes into peptides.

Main Methods:

  • Developed a synthetic strategy for on-resin peptide cyclization.
  • Employed thiol-ene photochemistry triggered by light.
  • Exploited the thiol group of natural cysteine amino acids.
  • Incorporated various alkenes orthogonal to the peptide backbone.

Main Results:

  • Achieved versatile and rapid on-resin cyclization of peptides.
  • Demonstrated the utility of thiol-ene photochemistry in peptide synthesis.
  • Successfully incorporated diverse alkenes into peptide structures.
  • The method is orthogonal to standard peptide synthesis.

Conclusions:

  • The developed thiol-ene photochemistry strategy offers a versatile and rapid approach for on-resin peptide cyclization.
  • This method provides a powerful tool for creating modified peptides with diverse functionalities.
  • The strategy is compatible with natural cysteine residues and allows for orthogonal alkene incorporation.