The Synthesis of 3-(R)- and 3-(S)-Hydroxyeicosapentaenoic Acid

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 ac...

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Autores principales: Gjessing, Gard, Johnsen, Lars-Inge Gammelsæter, Antonsen, Simen Gjelseth, Nolsøe, Jens M. J., Stenstrøm, Yngve, Hansen, Trond Vidar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9000449/
https://www.ncbi.nlm.nih.gov/pubmed/35408694
http://dx.doi.org/10.3390/molecules27072295
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author Gjessing, Gard
Johnsen, Lars-Inge Gammelsæter
Antonsen, Simen Gjelseth
Nolsøe, Jens M. J.
Stenstrøm, Yngve
Hansen, Trond Vidar
author_facet Gjessing, Gard
Johnsen, Lars-Inge Gammelsæter
Antonsen, Simen Gjelseth
Nolsøe, Jens M. J.
Stenstrøm, Yngve
Hansen, Trond Vidar
author_sort Gjessing, Gard
collection PubMed
description 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.
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spelling pubmed-90004492022-04-12 The Synthesis of 3-(R)- and 3-(S)-Hydroxyeicosapentaenoic Acid Gjessing, Gard Johnsen, Lars-Inge Gammelsæter Antonsen, Simen Gjelseth Nolsøe, Jens M. J. Stenstrøm, Yngve Hansen, Trond Vidar Molecules Article 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. MDPI 2022-04-01 /pmc/articles/PMC9000449/ /pubmed/35408694 http://dx.doi.org/10.3390/molecules27072295 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Gjessing, Gard
Johnsen, Lars-Inge Gammelsæter
Antonsen, Simen Gjelseth
Nolsøe, Jens M. J.
Stenstrøm, Yngve
Hansen, Trond Vidar
The Synthesis of 3-(R)- and 3-(S)-Hydroxyeicosapentaenoic Acid
title The Synthesis of 3-(R)- and 3-(S)-Hydroxyeicosapentaenoic Acid
title_full The Synthesis of 3-(R)- and 3-(S)-Hydroxyeicosapentaenoic Acid
title_fullStr The Synthesis of 3-(R)- and 3-(S)-Hydroxyeicosapentaenoic Acid
title_full_unstemmed The Synthesis of 3-(R)- and 3-(S)-Hydroxyeicosapentaenoic Acid
title_short The Synthesis of 3-(R)- and 3-(S)-Hydroxyeicosapentaenoic Acid
title_sort synthesis of 3-(r)- and 3-(s)-hydroxyeicosapentaenoic acid
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9000449/
https://www.ncbi.nlm.nih.gov/pubmed/35408694
http://dx.doi.org/10.3390/molecules27072295
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