Related Experiment Video
Updated: Jun 18, 2026

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
On the mechanism of microsomal prostaglandin E synthase type-2--a theoretical study of endoperoxide reaction with
Yi Li1, Michael Angelastro, Stephen Shimshock
1Discovery Research, sanofi-aventis, 1041 Route 202/206 N, Bridgewater, NJ 08807, USA. yi.li@sanofi-aventis.com
Abstract:
The reaction pathways of deprotonation versus nucleophilic substitution involving mPGES-2 enzyme catalysis were investigated by ab initio molecular orbital theory calculations for the reaction of methylthiolate with the endoperoxide core of PGH(2) and by the combined quantum mechanical molecular mechanical methods. The calculations showed that deprotonation mechanism is energetically more favorable than the nucleophilic substitution pathway.
Related Concept Videos
Preparation of Epoxides
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...
Drug Metabolism: Phase II Reactions
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Acid-Catalyzed Ring-Opening of Epoxides
Peroxisomes
Peroxisomes

