顺式-9-十八碳烯酰基辅酶 A 钾盐 | 1716-06-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 顺式-9-十八碳烯酰基辅酶 A 钾盐
• 中文别名: 顺式-9-十八碳烯酰基辅酶A钾盐；油酰辅酶A,钾盐
• 英文名称: oleoyl-CoA
• 英文别名: Oleoyl-Coenzyme A；[14C]-Oleoyl Coenzyme A；S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] (Z)-octadec-9-enethioate
• CAS: 1716-06-9
• 化学式: C₃₉H₆₈N₇O₁₇P₃S
• 分子量: 1031.99
• InChiKey: XDUHQPOXLUAVEE-BPMMELMSSA-N

物化性质

• 密度：
  1.51±0.1 g/cm3(Predicted)
• 物理描述：
  Solid
• 碰撞截面：
  299.4 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  67
• 可旋转键数：
  35
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  389
• 氢给体数：
  9
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  1-oleoyl-2-lyso-sn-glycero-3-phosphate 、 顺式-9-十八碳烯酰基辅酶 A 钾盐 在 乙二胺 乙二胺四乙酸 、 D-山梨糖 、 5,5'-二硫双(2-硝基苯甲酸) 作用下， 反应 0.02h， 生成 Dioleoylphosphatidic acid
  参考文献：
  名称：

  Biosynthesis of Castor Oil: Effect of Polyamines on the Acylation of Lysophosphatidic Acid at thesn-2 Position with Ricinoleic Acid

  摘要：

  链长超过 3C 的二胺结构的多胺对于通过蓖麻 LPA 酰基转移酶反应从蓖麻油酰辅酶 A 和溶血磷脂酸 (LPA) 合成磷脂酸 (PA) 至关重要，这表明多胺调节酶对酰基辅酶 A 底物的亲和力体内。

  DOI：

  10.1271/bbb.70044
• 作为产物：
  描述：

  、 三羟甲基氨基甲烷盐酸盐 、 5’-三磷酸腺苷 、 乙二胺四乙酸 、 sodium fluoride 、 N-[2-(Dimethylamino)ethyl]-2-(2-ethylbutoxy)-N-methyl-2,2-diphenylacetamide--hydrogen chloride (1/1) 、 、 辅酶 A 在 ice 、 辅酶 A 、 异丙醇 、 radioactive oleic acid 作用下， 反应 0.17h， 生成 顺式-9-十八碳烯酰基辅酶 A 钾盐
  参考文献：
  名称：

  Biorefinery system, methods and compositions thereof

  摘要：

  本公开涉及生物工程方法用于生产生物燃料，特别是使用C1代谢微生物反应器系统将C1底物（如甲烷或甲醇）转化为生物质，随后转化为生物燃料、生物塑料等。

  公开号：

  US09410168B2

文献信息

• Structural insights into the inhibition mechanism of human sterol O-acyltransferase 1 by a competitive inhibitor
  作者：Chengcheng Guan、Yange Niu、Si-Cong Chen、Yunlu Kang、Jing-Xiang Wu、Koji Nishi、Catherine C. Y. Chang、Ta-Yuan Chang、Tuoping Luo、Lei Chen

  DOI：10.1038/s41467-020-16288-4

  日期：——

  a target to treat several human diseases. However, its structure and mechanism remain elusive since its discovery. Here, we report the structure of human SOAT1 (hSOAT1) determined by cryo-EM. hSOAT1 is a tetramer consisted of a dimer of dimer. The structure of hSOAT1 dimer at 3.5 Å resolution reveals that a small molecule inhibitor CI-976 binds inside the catalytic chamber and blocks the accessibility

  甾醇 O-酰基转移酶 1 (SOAT1) 是内质网 (ER) 驻留的多跨膜酶，属于膜结合 O-酰基转移酶 (MBOAT) 家族。它催化胆固醇的酯化，生成用于储存胆固醇的胆固醇酯。SOAT1 是治疗多种人类疾病的目标。然而，自发现以来，其结构和机制仍然难以捉摸。在这里，我们报告了由冷冻电镜确定的人类 SOAT1 (hSOAT1) 的结构。hSOAT1 是由二聚体的二聚体组成的四聚体。分辨率为 3.5 Å 的 hSOAT1 二聚体的结构表明，小分子抑制剂 CI-976 在催化室内结合并阻止活性位点残基 H460、N421 和 W420 的可及性。
• BIOREFINERY SYSTEM, METHODS AND COMPOSITIONS THEREOF
  申请人：Calysta Energy, Inc.

  公开号：US20140013658A1

  公开（公告）日：2014-01-16

  The present disclosure relates to bioengineering approaches for producing biofuel and, in particular, to the use of a C 1 metabolizing microorganism reactor system for converting C 1 substrates, such as methane or methanol, into biomass and subsequently into biofuels, bioplastics, or the like.

  本公开涉及用于生产生物燃料的生物工程方法，特别是使用C1代谢微生物反应器系统将C1底物（如甲烷或甲醇）转化为生物质，随后转化为生物燃料、生物塑料或类似物的方法。
• Chemoselective Esterification of Natural and Prebiotic 1,2-Amino Alcohol Amphiphiles in Water
  作者：Ahanjit Bhattacharya、Lalita Tanwar、Alessandro Fracassi、Roberto J. Brea、Marta Salvador-Castell、Satyam Khanal、Sunil K. Sinha、Neal K. Devaraj

  DOI：10.1021/jacs.3c12038

  日期：2023.12.13

  enzyme-free esterification of amphiphiles in water and none that can occur in water at physiological pH using biochemically relevant acylating agents. Here we report the unexpected chemoselective O-acylation of 1,2-amino alcohol amphiphiles in water directed by Cu(II) and several other transition metal ions. In buffers containing Cu(II) ions, mixing biological 1,2-amino alcohol amphiphiles such as sphingosylphosphorylcholine

  在细胞中，大量的膜脂是通过极性头基与酰化剂（例如脂肪酰辅酶A）的酶促O-酰化形成的。尽管这种含酯的脂质似乎是地球上生命的必需品，但尚不清楚在生命起源时缺乏酶机制的情况下是否可以自发形成类似类型的脂质。两亲物在水中进行无酶酯化的例子很少，而且没有一个可以在生理 pH 值下使用生化相关酰化剂在水中发生的例子。在这里，我们报道了 Cu(II) 和其他几种过渡金属离子引导下的 1,2-氨基醇两亲物在水中发生意外的化学选择性 O-酰化。在含有 Cu(II) 离子的缓冲液中，将生物 1,2-氨基醇两亲物（例如鞘氨酰磷酰胆碱）与生化相关的酰化剂（即酰基腺苷酸和酰基辅酶 A）混合，可形成高选择性的 O-酰化产物。由此产生的 O-酰化鞘脂自组装成囊泡，其生物物理特性与由 N-酰基对应物形成的囊泡明显不同。我们还证明 Cu(II) 可以指导替代 1,2-氨基醇的 O-酰化，包括益生元相关的 1,2-氨基醇两亲
• Alkylresorcylic acid synthesis by type III polyketide synthases from rice Oryza sativa
  作者：Miku Matsuzawa、Yohei Katsuyama、Nobutaka Funa、Sueharu Horinouchi

  DOI：10.1016/j.phytochem.2010.02.012

  日期：2010.7

  Alkylresorcinols, produced by various plants, bacteria, and fungi, are bioactive compounds possessing beneficial activities for human health, such as anti-cancer activity. In rice, they accumulate in seedlings, contributing to protection against fungi. Alkylresorcylic acids, which are carboxylated forms of alkylresorcinols, are unstable compounds and decarboxylate readily to yield alkylresorcinols. Genome mining of the rice Oryza sativa identified two type III polyketide synthases, named ARAS1 (alkylresorcylic acid synthase) and ARAS2, that catalyze the formation of alkylresorcylic acids. Both enzymes condensed fatty acyl-CoAs with three C-2 units from malonyl-CoA and cyclized the resulting tetraketide intermediates via intramolecular C-2 to C-7 aldol condensation. The alkylresorcylic acids thus produced were released from the enzyme and decarboxylated non-enzymatically to yield alkylresorcinols. This is the first report on a plant type III polyketide synthase that produces tetraketide alkylresorcylic acids as major products. (C)2010 Published by Elsevier Ltd.
• CGI-58/ABHD5 is a coenzyme A-dependent lysophosphatidic acid acyltransferase
  作者：Gabriela Montero-Moran、Jorge M. Caviglia、Derek McMahon、Alexis Rothenberg、Vidya Subramanian、Zhi Xu、Samuel Lara-Gonzalez、Judith Storch、George M. Carman、Dawn L. Brasaemle

  DOI：10.1194/jlr.m001917

  日期：2010.4

  Mutations in human CGI-58/ABHD5 cause Chanarin-Dorfman syndrome (CDS), characterized by excessive storage of triacylglycerol in tissues. CGI-58 is an alpha/beta-hydrolase fold enzyme expressed in all vertebrates. The carboxyl terminus includes a highly conserved consensus sequence (HXXXXD) for acyltransferase activity. Mouse CGI-58 was expressed in Escherichia coli as a fusion protein with two amino terminal 6-histidine tags. Recombinant CGI-58 displayed acyl-CoA-dependent acyltransferase activity to lysophosphatidic acid, but not to other lysophospholipid or neutral glycerolipid acceptors. Production of phosphatidic acid increased with time and increasing concentrations of recombinant CGI-58 and was optimal between pH 7.0 and 8.5. The enzyme showed saturation kinetics with respect to 1-oleoyl-lysophosphatidic acid and oleoyl-CoA and preference for arachidonoyl-CoA and oleoyl-CoA. The enzyme showed slight preference for 1-oleoyl lysophosphatidic acid over 1-palmitoyl, 1-stearoyl, or 1-arachidonoyl lysophosphatidic acid. Recombinant CGI-58 showed intrinsic fluorescence for tryptophan that was quenched by the addition of 1-oleoyl-lysophosphatidic acid, oleoyl-CoA, arachidonoyl-CoA, and palmitoyl-CoA, but not by lysophosphatidyl choline. Expression of CGI-58 in fibroblasts from humans with CDS increased the incorporation of radiolabeled fatty acids released from the lipolysis of stored triacylglycerols into phospholipids. CGI-58 is a CoA-dependent lysophosphatidic acid acyltransferase that channels fatty acids released from the hydrolysis of stored triacylglycerols into phospholipids.-Montero-Moran, G., J. M. Caviglia, D. McMahon, A. Rothenberg, V. Suramanian, Z. Xu, S. Lara-Gonzalez, J. Storch, G. M. Carman, and D. L. Brasaemle. CGI-58/ABHD5 is a coenzyme A-dependent lysophosphatidic acid acyltransferase. J. Lipid Res. 2010. 51: 709-719.