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Total synthesis of 2‐methoxy‐14‐methylpentadecanoic acid and the novel 2‐methoxy‐14‐methylhexadecanoic acid identified in the sponge agelas dispar
Author(s) -
Carballeira Néstor M.,
Cruz Heidyleen,
Ayala Norma L.
Publication year - 2002
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-002-0997-9
Subject(s) - sponge , dispar , phospholipid , stereochemistry , chemistry , fatty acid , biochemistry , organic chemistry , biology , botany , microbiology and biotechnology , membrane , entamoeba histolytica
Abstract The phospholipid FA composition of the Carbbean sponge Agelas dispar was revisited and 40 different FA were identified. Among these a novel 2‐methoxylated FA, namely, the anteiso methyl‐branched 2‐methoxy‐14‐methylhexadecanoic acid, was identified together with the recently discovered iso methyl‐branched 2‐methoxy‐14‐methylpentadecanoic acid and the normal‐chain 2‐methoxytetradecanoic acid. The structures of the iso and anteiso methyl‐branched 2‐methoxylated FA were confirmed by total syntheses, which were accomplished in seven steps and in 45–48% overall yields. Other phospholipid FA identified in A. dispar include the unusual methyl‐branched 10, 130dimethyltetradecanoic acid, 3,7,11,15‐tetramethylhexadecanoic (phytanic) acid, and the 11‐methyloctadecanoic acid. In addition, the Δ 5,9 FA (5 Z , 9 Z )‐15‐methyl‐5,9‐hexadecadienoic acid and (5 Z , 9 Z )‐5,9‐octadecadienoic acid were characterized. These findings establish alternative FA biosynthetic possibilities for these marine organisms.