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Related Concept Videos

Sharpless Epoxidation02:57

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...
Preparation of Epoxides03:00

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...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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.
Base-Catalyzed Ring-Opening of Epoxides02:26

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...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

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Updated: May 14, 2026

X-Ray Crystallography to Study the Oligomeric State Transition of the Thermotoga maritima M42 Aminopeptidase TmPep1050
11:27

X-Ray Crystallography to Study the Oligomeric State Transition of the Thermotoga maritima M42 Aminopeptidase TmPep1050

Published on: May 13, 2020

Soluble epoxide hydrolase dimerization is required for hydrolase activity.

Jonathan W Nelson1, Rishi M Subrahmanyan2, Sol A Summers2

  • 1Departments of Anesthesiology and Perioperative Medicine, Oregon Health & Science University, Portland, Oregon 97239-3098; Molecular and Medical Genetics, Oregon Health & Science University, Portland, Oregon 97239-3098.

The Journal of Biological Chemistry
|January 31, 2013
PubMed
Summary

Soluble epoxide hydrolase (sEH) dimerization is essential for its enzymatic activity. Disrupting this dimerization may offer a new therapeutic strategy for cardiovascular diseases by inhibiting sEH function.

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Combining Non-reducing SDS-PAGE Analysis and Chemical Crosslinking to Detect Multimeric Complexes Stabilized by Disulfide Linkages in Mammalian Cells in Culture

Published on: May 2, 2019

Area of Science:

  • Biochemistry
  • Molecular Biology
  • Cardiovascular Research

Background:

  • Soluble epoxide hydrolase (sEH) metabolizes protective eicosanoids.
  • sEH inhibition is a therapeutic target for cardiovascular diseases.
  • A human polymorphism (R287Q) affects sEH activity and localization at the dimerization interface.

Purpose of the Study:

  • To investigate the direct relationship between sEH dimerization and its hydrolase activity.
  • To test the hypothesis that sEH dimerization is essential for its function.

Main Methods:

  • Engineered mutations to disrupt or stabilize sEH dimerization.
  • Quantified dimerization using a split firefly luciferase complementation assay.
  • Assessed hydrolase activity via a fluorescence-based substrate conversion assay.

Main Results:

  • Mutations disrupting dimerization abolished sEH hydrolase activity.
  • A mutation stabilizing dimerization restored hydrolase activity.
  • The R287Q polymorphism exhibited metastable dimerization kinetics.

Conclusions:

  • sEH dimerization is a prerequisite for its enzymatic activity.
  • Disrupting sEH dimerization represents a potential therapeutic strategy for cardiovascular conditions.
  • Targeting sEH dimerization could modulate its activity in disease contexts.