Related Experiment Video
Updated: Sep 27, 2025

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
The Synthesis of 3-(R)- and 3-(S)-Hydroxyeicosapentaenoic Acid
Gard Gjessing1, Lars-Inge Gammelsæter Johnsen2, Simen Gjelseth Antonsen1,3
1Department of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, NO-1433 Ås, Norway.
Abstract:
Monohydroxylated polyunsaturated fatty acids belonging to the oxylipin class of natural products are present in marine and terrestrial sources as well as in the human body. Due to their biological activities and role in diverse biosynthetic pathways, oxylipins biosynthesized from eicosapentaenoic acid and arachidonic acid have attracted great interest from the scientific community. One example is 3-hydroxyeicosapentaenoic acid where the absolute configuration at C-3 has only been tentatively assigned. In this paper, studies on acetate type aldol reactions that enabled the preparation of 3-(R)-hydroxyeicosapentaenoic acid (3R-HETE, 2) and its enantiomer are presented.
More Related Videos
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...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Naming Enantiomers
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Esters to Carboxylic Acids: Saponification
The reaction requires a base in stoichiometric amounts, which participates in the reaction and is not regenerated later. So, the base acts as a...

