trans-3-cis-5-octadienoyl-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: trans-3-cis-5-octadienoyl-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-[[3-[2-[(3E,5Z)-octa-3,5-dienoyl]sulfanylethylamino]-3-oxopropyl]amino]-4-oxobutoxy]-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]oxolan-3-yl] phosphate
• 化学式: C29H42N7O17P3S-4
• 分子量: 885.7
• InChiKey: XMHCCMXYCWOYHF-GRQFGQEHSA-J

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  57
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  trans-3-cis-5-octadienoyl-CoA(4-) 生成 trans,trans-octa-2,4-dienoyl-CoA(4-)
  参考文献：
  名称：

  Δ3,5,Δ2,4-Dienoyl-CoA Isomerase Is a Multifunctional Isomerase

  摘要：

  Delta (3,5),Delta (2,4)-Dienoyl-CoA isomerase (DI), an auxiliary enzyme of unsaturated fatty acid beta -oxidation, was purified from rat mitochondria and peroxisomes and subjected to N-terminal sequencing to facilitate a mechanistic study of this enzyme, The mature mitochondrial DI from rat heart was lacking its 34 N-terminal amino acid residues that have the properties of a mitochondrial targeting sequence. The peroxisomal isomerase was identified as a product of the same gene with a truncated and ragged N terminus. Expression of the cDNA coding for the mature mitochondrial DI in Escherichia coli yielded an enzyme preparation that was as active as the native DI, Because the recombinant DI also exhibited Delta (3,5,7)Delta (2,4,6)-trienoyl-CoA isomerase (TI) activity, both isomerases reside on the same protein, Mutations of any of the 3 acidic amino acid residues located at the active site (Modis, Y,, Filppula, S, A, Novikov, D, H., Norledge, B,, Hiltunen, J, K., and Wierenga, R, K, (1998) Structure 6, 957-970) caused activity losses. In contrast to only a 10-fold decrease in activity upon replacement of Asp(176) by Ala, substitutions of Asp(204) by Asn and of Glu(196) by Gin resulted in 10(5)-fold lower activities. Such activity losses are consistent with the direct involvement of these latter two residues in the proposed proton transfers at carbons 2 and 6 or 8 of the substrates, Probing of the wild-type and mutants forms of the enzyme with 2,5-octadienoyl-CoA as substrate revealed low Delta (2),Delta (3)- enoyl-CoA isomerase and Delta (5),Delta (4)-enoyl-CoA isomerase activities catalyzed by Glu(196) and Asp(204), respectively. Altogether, these data reveal that positional isomerizations of the diene and triene are facilitated by simultaneous proton transfers involving Glu(196) and Asp(204) whereas each residue alone can catalyze, albeit less efficiently, a monoene isomerization.

  DOI：

  10.1074/jbc.m011315200

文献信息

• Functional Characterization of Δ3,Δ2-Enoyl-CoA Isomerases from Rat Liver
  作者：Dongyan Zhang、Wenfeng Yu、Brian V. Geisbrecht、Stephen J. Gould、Howard Sprecher、Horst Schulz

  DOI：10.1074/jbc.m112228200

  日期：2002.3

  mitochondrial enoyl-CoA isomerase (MECI) in mitochondria, whereas peroxisomes contain ECI and multifunctional enzyme 1 (MFE1). Thus ECI, which previously had been described as peroxisomal enoyl-CoA isomerase, was found to be present in both peroxisomes and mitochondria. This enzyme seems to be identical with mitochondrial long-chain enoyl-CoA isomerase (Kilponen, J.M., Palosaari, P.M., and Hiltunen, J

  通过β-氧化降解不饱和脂肪酸涉及Delta（3），Delta（2）-烯酰-CoA异构酶（烯酰-CoA异构酶），可催化3-顺式-> 2-反式和3-反式-> 2烯酰-CoAs的-反式异构化和二烯丙基-CoAs的2,5-> 3,5异构化。对大鼠肝脏烯酰辅酶A异构酶的分析表明，线粒体中除了线粒体烯酰辅酶A异构酶（MECI）之外，还存在单官能烯酰辅酶A异构酶（ECI），而过氧化物酶体则包含ECI和多功能酶1（MFE1）。因此，以前被描述为过氧化物酶体烯酰-CoA异构酶的ECI被发现同时存在于过氧化物酶体和线粒体中。该酶似乎与线粒体长链烯酰基-CoA异构酶相同（Kilponen，JM，Palosaari，PM和Hiltunen，JK 1990.Biochem.J.269，223-226）。所有三种肝烯酰-CoA异构酶均具有宽链长特异性，但可通过其对三种异构化反应之一的偏好来区分。MECI在催化3-cis->