Journal of Organic Chemistry p. 2751 - 2756 (1986)
Update date:2022-09-26
Topics: Biosynthetic studies Experimental Studies Biosynthesis
Carballeira, Nestor
Thompson, Janice E.
Ayanoglu, Eser
Djerassi, Carl
The very long chain branched fatty acids 25-methyl-5,9-hexacosadienoic (Δ5,9-iso-27:2)-and 24-methyl-5,9-hexacosadienoic (Δ5,9-anteiso-27:2) acids as well as the straight-chain 5,9-hexacosadienoic (Δ5,9-26:2) acid were shown to originate from the short-chain precursors 13-methyltetradecanoic (iso-15:0), 12-methyltetradecanoic (anteiso-15:0), and palmitic (n-16:0) acids, respectively, by means of 14C incorporation experiments in the marine sponge Jaspis stellifera.These results confirm that methyl branching does not occur after chain elongation.The unusual Δ5,9 unsaturation probably takes place after chain elongation of short branched or straight-chain fatty acids.
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