cis-3-octenoyl-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: cis-3-octenoyl-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-[(Z)-oct-3-enoyl]sulfanylethylamino]-3-oxopropyl]amino]-4-oxobutoxy]-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]oxolan-3-yl] phosphate
• 化学式: C29H44N7O17P3S-4
• 分子量: 887.7
• InChiKey: CSCVMTFVEARIET-IJKSGAABSA-J

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  57
• 可旋转键数：
  24
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.66
• 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：

  cis-3-octenoyl-CoA(4-) 生成 (2E)-Octenoyl-CoA
  参考文献：
  名称：

  来自大鼠肝脏的Delta3，Delta2-enoyl-CoA异构酶的功能表征。

  摘要：

  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->

  DOI：

  10.1074/jbc.m112228200

文献信息

• Δ3, Δ2-enoyl-CoA isomerase is the protein that copurifies with human glutathione <i>S</i>-transferases from <i>S</i>-hexylglutathione affinity matrices
  作者：Y Takahashi、Y Hirata、Y Burstein、I Listowsky

  DOI：10.1042/bj3040849

  日期：1994.12.15

  An unidentified 30 kDa protein frequently copurifies with human glutathione S-transferases from S-hexyl-glutathione affinity matrices. Application of two-step sequential affinity chromatographic methods yielded a homogeneous preparation of that protein from human liver specimens. The protein was digested with Achromobacter protease I, and sequences of peptides resolved by h.p.l.c. showed a high degree

  未知的30 kDa蛋白经常与S-己基-谷胱甘肽亲和基质中的人谷胱甘肽S-转移酶共纯化。两步连续亲和色谱法的应用从人肝标本中均匀制备了该蛋白质。该蛋白质用无色杆菌蛋白酶I消化，并且hplc解析的肽序列与大鼠线粒体delta 3，delta 2-enoyl-CoA异构酶具有高度的同一性。人蛋白质还显示出以δ3-顺-辛烯基CoA为底物的催化活性。因此，它被鉴定为肝δ3，δ2-烯酰基-CoA异构酶。
• Characterization of PECI, a Novel Monofunctional Δ3,Δ2-Enoyl-CoA Isomerase of Mammalian Peroxisomes
  作者：Brian V. Geisbrecht、Dongyan Zhang、Horst Schulz、Stephen J. Gould

  DOI：10.1074/jbc.274.31.21797

  日期：1999.7

  We report here the identification and characterization of human and mouse PECI, a novel gene that encodes a monofunctional peroxisomal Delta(3),Delta(2)-enoyl-CoA isomerase, Human and mouse PECI were identified on the basis of their sequence similarity to Eci1p, a recently characterized peroxisomal Delta(3),Delta(2)-enoyl-CoA isomerase from the yeast Saccharomyces cerevisiae. Cloning and sequencing of the human PECI cDNA revealed the presence of a 1077-base pair open reading frame predicted to encode a 359-amino acid protein with a mass of 39.6 kDa. The corresponding mouse cDNA contains a 1074-base pair open reading frame that encodes a 358-amino acid-long protein with a deduced mass of 39.4 kDa, Northern blot analysis demonstrated human PECI mRNA is expressed in all tissues. A bacterially expressed form of human PECI catalyzed the isomerization of 3-cis-octenoyl-CoA to 2-trans-octenoyl-CoA with a specific activity of 27 units/mg of protein. The human and mouse PECI proteins contain type-1 peroxisomal targeting signals, and human PECI was localized to peroxisomes by both subcellular fractionation and immunofluorescence microscopy techniques. The potential roles for this monofunctional Delta(3),Delta(2)-enoyl-CoA isomerase in peroxisomal metabolism are discussed.