(5Z)-tetradecenoyl-CoA(4-)

• 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: (5Z)-tetradecenoyl-CoA(4-)
• 英文别名: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[[[[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-[2-[(Z)-tetradec-5-enoyl]sulfanylethylamino]propyl]amino]butoxy]-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]oxolan-3-yl] phosphate
• 化学式: C35H56N7O17P3S-4
• 分子量: 971.8
• InChiKey: MRVDZOHJMLTLHJ-STFCKWFXSA-J

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  63
• 可旋转键数：
  30
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  400
• 氢给体数：
  5
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  (5Z)-tetradecenoyl-CoA(4-) 、 左旋肉碱 生成 coenzyme A 、 5-顺式十四烷肉碱
  参考文献：
  名称：

  肉碱棕榈酰转移酶2：对底物特异性及其对酰基肉碱谱分析的启示。

  摘要：

  近年来，酰基肉碱已成为诊断线粒体脂肪酸β-氧化（mFAO）和支链氨基酸氧化障碍的重要生物标志物，前提是它们反映了潜在的毒性酰基辅酶A物种，在线粒体内积累在酶嵌段的上游。但是，这些中间体的起源仍然知之甚少。肉碱航天飞机成员肉碱棕榈酰转移酶2（CPT2）可能参与了线粒体内由积累的酰基CoA代谢产物合成的酰基肉碱。为了解决这个问题，本文研究了CPT2的底物特异性概况。将表达人CPT2的啤酒酵母匀浆与饱和和不饱和的C2-C26酰基辅酶A和支链氨基酸氧化中间体孵育。通过ESI-MS / MS对产生的酰基肉碱进行定量。我们显示CPT2与中等（C8-C12）和长链（C14-C18）酰基辅酶A酯具有活性，而实际上未发现短链和长链酰基辅酶A或支链氨基具有活性酸氧化中间体。还发现反式-2-烯酰基-CoA中间体是CPT2的不良底物。进行的抑制研究表明，trans-2-C16：1-CoA可以作为CPT2的竞争性抑制剂（K（i）为18

  DOI：

  10.1016/j.bbadis.2010.06.002
• 作为产物：
  描述：

  (7Z)-3-oxohexadecenoyl-CoA(4-) 、 coenzyme A 生成 (5Z)-tetradecenoyl-CoA(4-) 、 (2R)-N-[3-(2-acetylsulfanylethylimino)-3-oxidopropyl]-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonatooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanimidate
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• Leaky β-Oxidation of a trans-Fatty Acid
  作者：Wenfeng Yu、Xiquan Liang、Regina E. Ensenauer、Jerry Vockley、Lawrence Sweetman、Horst Schulz

  DOI：10.1074/jbc.m409640200

  日期：2004.12

  The degradation of elaidic acid (9-trans-octadecenoic acid), oleic acid, and stearic acid by rat mitochondria was studied to determine whether the presence of a trans double bond in place of a cis double bond or no double bond affects beta-oxidation. Rat mitochondria from liver or heart effectively degraded the coenzyme A derivatives of all three fatty acids. However, with elaidoyl-CoA as a substrate, a major metabolite accumulated in the mitochondrial matrix. This metabolite was isolated and identified as 5-trans-tetradecenoyl-CoA. In contrast, little or none of the corresponding metabolites were detected with oleoyl-CoA or stearoyl-CoA as substrates. A kinetic study of long-chain acyl-CoA dehydrogenase (LCAD) and very long-chain acyl-CoA dehydrogenase revealed that 5-trans-tetradecenoyl-CoA is a poorer substrate of LCAD than is 5-cis-tetradecenoyl-CoA, while both unsaturated acyl-CoAs are poor substrates of very long-chain acyl-CoA dehydrogenase when compared with myristoyl-CoA. Tetradecenoic acid and tetradecenoylcarnitine were detected by gas chromatography/ mass spectrometry and tandem mass spectrometry, respectively, when rat liver mitochondria were incubated with elaidoyl-CoA but not when oleoyl-CoA was the substrate. These observations support the conclusion that 5-trans-tetradecenoyl-CoA accumulates in the mitochondrial matrix, because it is less efficiently dehydrogenated by LCAD than is its cis isomer and that the accumulation of this beta-oxidation intermediate facilitates its hydrolysis and conversion to 5-trans-tetradecenoylcarnitine thereby permitting a partially degraded fatty acid to escape from mitochondria. Analysis of this compromised but functional process provides insight into the operation of beta-oxidation in intact mitochondria.