trans-11,cis-15-octadecadienoic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: trans-11,cis-15-octadecadienoic acid
• 英文别名: Vaccelenic acid；(11E,15Z)-octadeca-11,15-dienoic acid
• 化学式: C₁₈H₃₂O₂
• 分子量: 280.451
• InChiKey: HHELYEVVXBEXIZ-ODYTWBPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Γ-十八碳三烯酸 在 Clostridium bifermentans JCM 1386 作用下， 生成 trans-11,cis-15-octadecadienoic acid
  参考文献：
  名称：

  Biohydrogenation of C20 polyunsaturated fatty acids by anaerobic bacteria

  摘要：

  The PUFAs include many bioactive lipids. The microbial metabolism of C-18 PUFAs is known to produce their bioactive isomers, such as conjugated FAs and hydroxy FAs, but there is little information on that of C-20 PUFAs. In this study, we aimed to obtain anaerobic bacteria with the ability to produce novel PUFAs from C-20 PUFAs. Through the screening of similar to 100 strains of anaerobic bacteria, Clostridium bifermentans JCM 1386 was selected as a strain with the ability to saturate PUFAs during anaerobic cultivation. This strain converted arachidonic acid (cis-5, cis-8, cis-11, cis-14-eicosatetraenoic acid) and EPA (cis-5, cis-8, cis-11, cis-14, cis-17-EPA) into cis-5, cis-8, trans-13-eicosatrienoic acid and cis-5, cis-8, trans-13, cis-17-eicosatetraenoic acid, giving yields of 57% and 67% against the added PUFAs, respectively. This is the first report of the isolation of a bacterium transforming C-20 PUFAs into corresponding non-methylene-interrupted FAs. We further investigated the substrate specificity of the biohydrogenation by this strain and revealed that it can convert two cis double bonds at the omega 6 and omega 9 positions in various C-18 and C-20 PUFAs into a trans double bond at the omega 7 position. jlr This study should serve to open up the development of novel potentially bioactive PUFAs.

  DOI：

  10.1194/jlr.m045450

文献信息

• HAMMOND, R. C., FETT. WISS TECHNOL., 90,(1988) N 1, 18-27
  作者：HAMMOND, R. C.

  DOI：——

  日期：——