Biosynthetic studies of marine lipids. 17. The course of chain elongation and desaturation in long-chain fatty acids of marine sponges

Biosynthetic studies of marine lipids. 17. The course of chain elongation and desaturation in long-chain fatty acids of marine sponges

Through appropriate labeling and incorporation experiments, the biosynthesis of the most characteristic sponge fatty acids, (5Z,9Z)-5,9-hexacosadienoic acid ( Delta super(5,9)-26:2) and (5Z,9Z,19Z)-5,9,19-hexacosatrienoic acid ( Delta super(5,9,19)-26:3), was completely elucidated. The dienoic acid...

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Veröffentlicht in:Journal of the American Chemical Society 1988-11, Vol.110 (24), p.8117-8124
Hauptverfasser: Hahn, Soonkap, Stoilov, Ivan L, Ha, T. B. Tam, Raederstorff, Daniel, Doss, George A, Li, Hui Ting, Djerassi, Carl
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Marine
Porifera
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container_end_page 8124
container_issue 24
container_start_page 8117
container_title Journal of the American Chemical Society
container_volume 110
creator Hahn, Soonkap
Stoilov, Ivan L
Ha, T. B. Tam
Raederstorff, Daniel
Doss, George A
Li, Hui Ting
Djerassi, Carl
description Through appropriate labeling and incorporation experiments, the biosynthesis of the most characteristic sponge fatty acids, (5Z,9Z)-5,9-hexacosadienoic acid ( Delta super(5,9)-26:2) and (5Z,9Z,19Z)-5,9,19-hexacosatrienoic acid ( Delta super(5,9,19)-26:3), was completely elucidated. The dienoic acid is produced by the sequence 14:0 arrow right arrow right 26:0 arrow right 26:1 arrow right 26:2. Contrary to precedent in animal fatty acid biosynthesis, the first desaturation occurs both at Delta super(5) and Delta super(9). The sponge secures palmitoleic acid ( Delta super(9)-16:1) from an exogenous source (bacteria?) and undergoes chain elongation to Delta super(19)-26:1 before undergoing Delta super(9)- and Delta super(5)-desaturation.
doi_str_mv 10.1021/ja00232a025
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Porifera
title Biosynthetic studies of marine lipids. 17. The course of chain elongation and desaturation in long-chain fatty acids of marine sponges
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