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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.5K
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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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.2K
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.
3.2K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.1K
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.
4.1K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.1K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
2.1K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.8K
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.
2.8K
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

9.5K
Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
9.5K

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Optimizing the Genetic Incorporation of Chemical Probes into GPCRs for Photo-crosslinking Mapping and Bioorthogonal Chemistry in Live Mammalian Cells
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Optimizing the Genetic Incorporation of Chemical Probes into GPCRs for Photo-crosslinking Mapping and Bioorthogonal Chemistry in Live Mammalian Cells

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Chemically triggered crosslinking with bioorthogonal cyclopropenones.

R David Row1, Sean S Nguyen1, Andrew J Ferreira1

  • 1Department of Chemistry, University of California, Irvine, California 92697, USA. jpresche@uci.edu.

Chemical Communications (Cambridge, England)
|August 19, 2020
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Summary

We developed a new bioorthogonal crosslinking method using cyclopropenones. This technique allows for the study of protein-protein interactions by forming covalent adducts in cell lysate.

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Area of Science:

  • Chemical Biology
  • Biochemistry

Background:

  • Studying biomolecular interactions is crucial in biology.
  • Existing crosslinking methods have limitations in scope and application.

Purpose of the Study:

  • To develop a novel proximity-driven crosslinking strategy.
  • To utilize bioorthogonal cyclopropenones for covalent adduct formation.

Main Methods:

  • Employing cyclopropenones that react with phosphines to generate ketene-ylides.
  • Utilizing these intermediates for trapping neighboring proteins.
  • Demonstrating crosslinking with a model split reporter system.
  • Testing the reaction in cell lysate.

Main Results:

  • Successful covalent adduct formation between proteins.
  • Tunable crosslinking rates achieved by varying phosphine triggers.
  • Demonstrated feasibility of the method in a complex biological environment (cell lysate).

Conclusions:

  • Cyclopropenones offer a versatile platform for proximity-driven crosslinking.
  • This strategy enables new approaches for studying biomolecular interactions.
  • The method shows potential for investigating protein-protein interactions and other molecular associations.