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Related Concept Videos

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.1K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

1.7K
Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
1.7K
Radical Formation: Overview01:03

Radical Formation: Overview

2.1K
A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...
2.1K
Radical Formation: Addition00:47

Radical Formation: Addition

1.7K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
1.7K
Radical Formation: Abstraction00:47

Radical Formation: Abstraction

3.5K
The electron of an atom can be abstracted from a compound by a relatively unstable radical to generate a new radical of relatively greater stability. For example, an initiator which forms radicals by homolysis can abstract a suitable species like a hydrogen atom or a halogen atom from a compound to generate a new radical. This ability of radicals to propagate by abstraction is a crucial feature of radical chain reactions.
Even though homolysis produces radicals, it is different from radical...
3.5K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.1K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.1K

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Updated: Jul 11, 2025

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

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P450-catalyzed atom transfer radical cyclization.

Heyu Chen1, Wenzhen Fu1, Yang Yang2

  • 1Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA, United States.

Methods in Enzymology
|November 17, 2023
PubMed
Summary
This summary is machine-generated.

Researchers developed directed evolution methods for P450 enzymes, enabling stereoselective biocatalytic atom transfer radical cyclization (ATRC). This breakthrough offers precise control over radical intermediates for advanced organic synthesis and catalysis.

Keywords:
Asymmetric catalysisAtom transfer radical cyclizationDirected evolutionP450

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Area of Science:

  • Biocatalysis
  • Enzymology
  • Organic Chemistry

Background:

  • Cytochromes P450 are versatile enzymes with broad applications in fundamental research and biotechnology.
  • Recent advances integrate synthetic organic chemistry principles to expand P450 catalytic capabilities beyond natural reactions.
  • This includes developing novel P450-catalyzed reactions for challenging organic synthesis problems.

Purpose of the Study:

  • To describe experimental protocols for the directed evolution of P450 enzymes into atom transfer radical cyclases.
  • To present detailed methods for both analytical and preparative scale biocatalytic atom transfer radical cyclization (ATRC).
  • To facilitate the development of new P450-mediated radical reactions and other synthetic processes.

Main Methods:

  • Utilizing directed evolution strategies inspired by synthetic organic chemistry.
  • Repurposing and evolving P450 enzymes to catalyze specific reactions.
  • Developing stereoselective biocatalytic atom transfer radical cyclization (ATRC) for radical intermediate control.

Main Results:

  • Successful directed evolution of P450 enzymes for biocatalytic ATRC.
  • Established protocols for implementing stereoselective ATRC using engineered P450s.
  • Demonstrated the potential for precise stereocontrol over transient free radical intermediates.

Conclusions:

  • Directed evolution of P450s provides a powerful platform for creating novel biocatalytic transformations.
  • Biocatalytic ATRC offers a new stereoselective approach for radical chemistry.
  • These developed methods will advance P450-catalyzed radical reactions and synthetic organic chemistry.