4.6 Article

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

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MOLECULES
卷 27, 期 7, 页码 -

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MDPI
DOI: 10.3390/molecules27072295

关键词

3-hydroxy eicosapentaenoic acid; eicosanoids; Nagao-Fujita acetate aldol reaction; Braun acetate aldol reaction; eicosapentaenoic acid; docosahexaenoic acid; oxylipins; F-19 NMR Mosher esters analysis; stereoselective synthesis

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  1. Department of Pharmacy

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Monohydroxylated polyunsaturated fatty acids are natural compounds found in marine, terrestrial, and human sources. They have attracted significant interest due to their biological activities and role in biosynthetic pathways. This paper presents the preparation of 3-(R)-hydroxyeicosapentaenoic acid and its enantiomer through acetate type aldol reactions.
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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