Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Preparation of Epoxides

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...

Base-Catalyzed Ring-Opening of Epoxides

Base-Catalyzed Ring-Opening of Epoxides

Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...

Acid-Catalyzed Ring-Opening of Epoxides

Acid-Catalyzed Ring-Opening of Epoxides

Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

Sharpless Epoxidation

Sharpless Epoxidation

The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...

Structure and Nomenclature of Epoxides

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

High-Throughput Prediction of Protein-Protein Interactions Uncovers Hidden Molecular Networks in Biosynthetic Gene Clusters.

Computational and structural biotechnology journal·2026

Same author

Non-Enzymatic Formation of Chaxines and Natural Steroidal Derivatives via Ergosterol Air Oxidation.

The Journal of organic chemistry·2026

Same author

Altered flagellin-TLR5 signaling pathway in interaction between host and laboratory Escherichia coli strains engineered for enhanced intestinal colonization in mouse.

Bioscience, biotechnology, and biochemistry·2026

Same author

Conformationally Defined Alkaloidal Building Units for the Controlled Formation of Nanoscale Supramolecular Morphologies.

Chemistry, an Asian journal·2026

Same author

Design and concise synthesis of halicyclamine-inspired bis-macrocycles targeting DedA membrane proteins.

Chemical communications (Cambridge, England)·2026

Same author

A system of paired polyether epoxide hydrolases enables a mouldable enzyme for consecutive ring cyclization cascades.

Nature chemistry·2026

Search research articles

Related Experiment Video

Updated: May 23, 2026

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids

Published on: June 28, 2019

Sequential enzymatic epoxidation involved in polyether lasalocid biosynthesis.

Atsushi Minami¹, Mayu Shimaya, Gaku Suzuki

¹Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.

Journal of the American Chemical Society

|April 18, 2012

Summary

Flavin-containing monooxygenases (FMOs) catalyze enantioselective epoxidation, a key step in constructing polyether skeletons like lasalocid. This study elucidates the enzymatic mechanism of polyether biosynthesis.

More Related Videos

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Published on: February 16, 2018

Preparation of Monodomain Liquid Crystal Elastomers and Liquid Crystal Elastomer Nanocomposites

Preparation of Monodomain Liquid Crystal Elastomers and Liquid Crystal Elastomer Nanocomposites

Published on: February 6, 2016

Related Experiment Videos

Last Updated: May 23, 2026

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids

Published on: June 28, 2019

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Published on: February 16, 2018

Preparation of Monodomain Liquid Crystal Elastomers and Liquid Crystal Elastomer Nanocomposites

Preparation of Monodomain Liquid Crystal Elastomers and Liquid Crystal Elastomer Nanocomposites

Published on: February 6, 2016

Area of Science:

Biochemistry
Organic Chemistry
Molecular Biology

Background:

Polyether skeletons are crucial in natural products like ionophore polyethers.
Enantioselective epoxidation and regioselective epoxide opening are key synthetic steps.
Flavin-containing monooxygenases (FMOs) are potential enzymes for oxidation in polyether biosynthesis.

Purpose of the Study:

To investigate the role of Lsd18, an FMO, in the biosynthesis of the polyether lasalocid.
To understand the enzymatic mechanism of enantioselective epoxidation in polyether construction.

Main Methods:

In vivo and in vitro analyses of the Lsd18 enzyme.
Use of substrate mimics, including simple olefins and truncated dienes.
Characterization of epoxidation products.

Main Results:

Lsd18 performs enantioselective epoxidation in a stepwise manner.
The enzyme produces natural-type mono- or bis-epoxides.
Demonstrated the involvement of FMOs in lasalocid polyether biosynthesis.

Conclusions:

Lsd18, a flavin-containing monooxygenase, is crucial for lasalocid biosynthesis.
The study clarifies the enzymatic pathway for constructing polyether skeletons.
Provides insights into the stepwise enantioselective epoxidation mechanism.