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

Molecules (Basel, Switzerland), 2022-04, Vol.27 (7), p.2295 [Peer Reviewed Journal]

2022 by the authors. 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/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. ;info:eu-repo/semantics/openAccess ;2022 by the authors. 2022 ;ISSN: 1420-3049 ;EISSN: 1420-3049 ;DOI: 10.3390/molecules27072295 ;PMID: 35408694

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Title:
The Synthesis of 3-( R )- and 3-( S )-Hydroxyeicosapentaenoic Acid
Author: Gjessing, Gard ; Johnsen, Lars-Inge Gammelsæter ; Antonsen, Simen Gjelseth ; Nolsøe, Jens M J ; Stenstrøm, Yngve ; Hansen, Trond Vidar
Subjects: 3-hydroxy eicosapentaenoic acid ; Absolute configuration ; Acetic acid ; Aldehydes ; Arachidonic Acid ; Braun acetate aldol reaction ; Chromatography ; docosahexaenoic acid ; eicosanoids ; Eicosapentaenoic Acid ; Enantiomers ; Fatty acids ; Fatty Acids, Unsaturated - metabolism ; Humans ; Investigations ; Nagao–Fujita acetate aldol reaction ; Natural products ; Oxylipins - metabolism ; Polyunsaturated fatty acids ; Spectrum analysis ; Stereoisomerism ; Terrestrial environments
Is Part Of: Molecules (Basel, Switzerland), 2022-04, Vol.27 (7), p.2295
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-( )-hydroxyeicosapentaenoic acid (3R-HETE, ) and its enantiomer are presented.
Publisher: Switzerland: MDPI AG
Language: English;Norwegian
Identifier: ISSN: 1420-3049
EISSN: 1420-3049
DOI: 10.3390/molecules27072295
PMID: 35408694
Source: GFMER Free Medical Journals
MEDLINE
NORA Norwegian Open Research Archives
PubMed Central
Alma/SFX Local Collection
ProQuest Central
DOAJ Directory of Open Access Journals

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

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