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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.0K
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.
2.0K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.5K
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.
2.5K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.8K
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
1.8K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.5K
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.
3.5K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.3K
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.
2.3K
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

8.2K
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...
8.2K

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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Redox-Activated Substrates for Enhancing Activatable Cyclopropene Bioorthogonal Reactions.

Wei-Siang Kao1, Wei Huang1, Yunlei Zhang1

  • 1Department of Chemistry, Stony Brook University, 100 Nicolls Road, Stony Brook, NY-11794, USA.

Chembiochem : a European Journal of Chemical Biology
|August 25, 2024
PubMed
Summary
This summary is machine-generated.

Researchers developed a faster bioorthogonal reaction using cyclopropene-quinone pairs for chemical biology applications. This new system offers enhanced reactivity and controllable activation for potential use in cellular imaging.

Keywords:
Bioorthogonal chemistryClick chemistryCycloadditionCyclopropene

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Area of Science:

  • Chemical Biology
  • Bioorthogonal Chemistry
  • Organic Synthesis

Background:

  • Bioorthogonal chemistry is crucial for chemical biology and clinical applications.
  • Designing selective, reactive, and stable bioorthogonal reagents is a key challenge.
  • Recent advances include controllable reactivity and click-and-release functionalities.

Purpose of the Study:

  • To improve the reactivity of a previously developed controllable cyclopropene-based bioorthogonal ligation.
  • To explore new diene reaction partners for cyclopropene reagents.
  • To investigate orthogonal activation mechanisms for enhanced bioorthogonal systems.

Main Methods:

  • Screening of diene reaction partners for cyclopropene reagents.
  • Kinetic analysis of cyclopropene-quinone ligation compared to tetrazine reactions.
  • Demonstration of orthogonal activation via caging group removal and redox control.
  • Application in live-cell imaging of cell membranes.

Main Results:

  • A cyclopropene-quinone pair exhibited a 26-fold increase in reaction rate compared to tetrazine ligations.
  • The cyclopropene-quinone reaction demonstrated dual orthogonal activation mechanisms.
  • The system was successfully employed for imaging fixed cell membranes.

Conclusions:

  • The cyclopropene-quinone ligation offers significantly enhanced reactivity for bioorthogonal applications.
  • Orthogonal activation strategies provide versatile control over bioorthogonal reactions.
  • This system shows promise as a bioimaging tool for cellular labeling.