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Related Concept Videos

Radical Formation: Addition00:47

Radical Formation: Addition

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 unpaired...
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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 molecule. These three...
Radical Formation: Overview01:03

Radical Formation: Overview

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 latter, also known...
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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 instance, consider...
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a low‐energy SOMO, which interacts...
Radical Formation: Elimination00:51

Radical Formation: Elimination

Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions with respect to...

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Related Experiment Video

Updated: May 22, 2026

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

Published on: April 15, 2013

Thioether crosslinkages created by a radical SAM enzyme.

Qi Zhang1, Yi Yu

  • 1Key Laboratory of Combinatory Biosynthesis and Drug Discovery (Ministry of Education) and School of Pharmaceutical Sciences, Wuhan University, 185 East Lake Road, Wuhan 430071, PR China. qizhang@sioc.ac.cn

Chembiochem : a European Journal of Chemical Biology
|May 5, 2012
PubMed
Summary

The enzyme AlbA uses radical S-adenosylmethionine chemistry to create unique sulfur-to-alpha-carbon thioether bonds in subtilosin A. This discovery reveals novel versatility in natural product biosynthesis and post-translational modifications.

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The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
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Last Updated: May 22, 2026

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

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Published on: April 15, 2013

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

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07:02

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry

Published on: August 25, 2016

Area of Science:

  • Biochemistry
  • Natural Product Biosynthesis
  • Enzymology

Background:

  • Lantibiotics feature well-characterized beta-carbon thioether linkages.
  • Post-translational modifications are crucial for generating diverse natural products.

Purpose of the Study:

  • To elucidate the mechanism behind the unusual sulfur-to-alpha-carbon thioether crosslinks in subtilosin A.
  • To characterize the enzyme responsible for these modifications and its catalytic machinery.

Main Methods:

  • Biochemical assays to study enzyme activity.
  • Structural analysis of the radical SAM enzyme AlbA.
  • Characterization of the [4Fe-4S] clusters within AlbA.

Main Results:

  • The radical SAM enzyme AlbA catalyzes the formation of sulfur-to-alpha-carbon thioether crosslinks in subtilosin A.
  • AlbA contains two distinct [4Fe-4S] clusters essential for its function.
  • This represents a novel pathway for thioether bond formation in natural product biosynthesis.

Conclusions:

  • The findings highlight the remarkable versatility of post-translational modifications in generating complex natural products.
  • The characterization of AlbA expands our understanding of radical SAM enzyme mechanisms.
  • Subtilosin A biosynthesis provides a new paradigm for sulfur-to-alpha-carbon thioether formation.