PHOSPHOLIPID STUDIES OF MARINE ORGANISMS .22. STRUCTURE AND BIOSYNTHESIS OF A NOVEL BROMINATED FATTY-ACID FROM A HYMENIACIDONID SPONGE
PHOSPHOLIPID STUDIES OF MARINE ORGANISMS .22. STRUCTURE AND BIOSYNTHESIS OF A NOVEL BROMINATED FATTY-ACID FROM A HYMENIACIDONID SPONGE
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DOI：
10.1021/jo00275a032
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发表时间：
1989-07-07
影响因子：
3.6
通讯作者：
DJERASSI, C
中科院分区：
文献类型：
--
作者：
LAM, WK;HAHN, SK;DJERASSI, C
从膜藻科海绵磷脂中分离得到一种新的长链脂肪酸(5E，9Z)-6-溴-5，9-六碳二烯酸(1a)。通过质谱学和2D-同核(COSY-45)1H核磁共振波谱对其结构进行了鉴定。溴代双键的构型是通过锂离子和质子化反应确定的。放射性标记前体的掺入实验表明，生物溴化是这种不寻常的酸生物合成的最后一步。
A new long-chain fatty acid, (5E,9Z)-6-bromo-5,9-hexacosadienoic acid (1a), was isolated from the phospholipids of a marine sponge of the family Hymeniacidonidae. Structure elucidation was accomplished by means of mass spectrometry and 2D-homonuclear (COSY-45) 1H NMR spectroscopy. The configuration of the bromo-substituted double bond was established by lithiation followed by protonolysis. Incorporation experiments with radiolabeled precursors revealed that biological bromination was the terminal step in the biosynthesis of this unusual acid.