(10S)-hydroperoxy-(8E)-octadecenoic acid | 126873-54-9

• 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: (10S)-hydroperoxy-(8E)-octadecenoic acid
• 英文别名: (10S)-HPOME；10S-hydroperoxy-8E-octadecenoic acid；(E,10S)-10-hydroperoxyoctadec-8-enoic acid
• CAS: 126873-54-9
• 化学式: C₁₈H₃₄O₄
• 分子量: 314.466
• InChiKey: HTIQDCPWTUODDW-VMEIHUARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  油酸 在 氧气 作用下， 以 水 为溶剂， 生成 (10S)-hydroperoxy-(8E)-octadecenoic acid 、 (7S,10S)-7,10-dihydroxy-octadec-8-enoic acid
  参考文献：
  名称：

  铜绿假单胞菌 42A2 的双加氧酶和氢过氧化物异构酶氧化不饱和脂肪酸的生化特征。

  摘要：

  我们研究了铜绿假单胞菌 42A2 细胞提取物对脂肪酸的氧化作用。油酸（(9Z)-18:1）转化为（10S）-氢过氧-（8E）-十八碳烯酸（（10S）-HPOME）和（7S，10S）-二羟基-（8E）-十八碳烯酸（ 7,10-DiHOME)。在oxy-18下的实验表明，7,10-DiHOME含有空气中的氧，并且由(10S)-HPOME通过异构化顺序形成。 (10R)-HPOME 未异构化。 (10S)-双加氧酶和氢过氧化物异构酶活性在离子交换色谱和凝胶过滤上共洗脱，表观分子大小约为 50 kDa。 16:1n-7、18:2n-6和20:1n-11也被氧化成7,10-二羟基脂肪酸，(8Z)-18:1被氧化成6,9-二羟基-(7E) -十八碳烯酸。一系列双键位置更靠近（(6Z)-18:1、(5Z,9Z)-18:2）或更远离羧基的脂肪酸（(11Z)-、(13Z)-和(15Z)-18:1) 是较差的

  DOI：

  10.1074/jbc.m109.078147

文献信息

• Stereoselective oxidation of regioisomeric octadecenoic acids by fatty acid dioxygenases
  作者：Ernst H. Oliw、Anneli Wennman、Inga Hoffmann、Ulrike Garscha、Mats Hamberg、Fredrik Jernerén

  DOI：10.1194/jlr.m018259

  日期：2011.11

  Seven Z-octadecenoic acids having the double bond located in positions 6Z to 13Z were photooxidized. The resulting hydroperoxy-E-octadecenoic acids [HpOME(E)] were resolved by chiral phase-HPLC-MS, and the absolute configurations of the enantiomers were determined by gas chromatographic analysis of diastereoisomeric derivatives. The MS/MS/MS spectra showed characteristic fragments, which were influenced by the distance between the hydroperoxide and carboxyl groups. These fatty acids were then investigated as substrates of cyclooxygenase-1 (COX-1), manganese lipoxygenase (MnLOX), and the (8R)-dioxygenase (8R-DOX) activities of two linoleate diol synthases (LDS) and 10R-DOX. COX-1 and MnLOX abstracted hydrogen at C-11 of (12Z)-18:1 and C-12 of (13Z)-18:1. (11Z)-18:1 was subject to hydrogen abstraction at C-10 by MnLOX and at both allylic positions by COX-1. Both allylic hydrogens of (8Z)-18:1 were also abstracted by 8R-DOX activities of LDS and 10R-DOX, but only the allylic hydrogens close to the carboxyl groups of (11Z)-18:1 and (12Z)-18:1. 8R-DOX also oxidized monoenoic C-14-C-20 fatty acids with double bonds at the (9Z) position, suggesting that the length of the omega end has little influence on positioning for oxygenation. We conclude that COX-1 and MnLOX can readily abstract allylic hydrogens of octadecenoic fatty acids from C-10 to C-12 and 8R-DOX from C-7 and C-12.-Oliw, E. H., A. Wennman, I. Hoffmann, U. Garscha, M. Hamberg, and F. Jerneren. Stereoselective oxidation of regioisomeric octadecenoic acids by fatty acid dioxygenases. J. Lipid Res. 2011. 52: 1995-2004.
• Biochemical Characterization of the Oxygenation of Unsaturated Fatty Acids by the Dioxygenase and Hydroperoxide Isomerase of Pseudomonas aeruginosa 42A2
  作者：Eriel Martínez、Mats Hamberg、Montse Busquets、Pilar Díaz、Angeles Manresa、Ernst H. Oliw

  DOI：10.1074/jbc.m109.078147

  日期：2010.3

  hydrogen at C-8 was lost in the biosynthesis of (10S)-HPODE, whereas the pro-S hydrogen was lost and the pro-R hydrogen was retained at C-7 during biosynthesis of the 7,10-dihydroxy metabolites. Analysis of the fatty acid composition of P. aeruginosa revealed relatively large amounts of (9E/Z)-16:1 and (11E/Z)-18:1 and only traces of 18:1n-9. We found that (11Z)-18:1 (vaccenic acid) was transformed to (11S

  我们研究了铜绿假单胞菌 42A2 细胞提取物对脂肪酸的氧化作用。油酸（(9Z)-18:1）转化为（10S）-氢过氧-（8E）-十八碳烯酸（（10S）-HPOME）和（7S，10S）-二羟基-（8E）-十八碳烯酸（ 7,10-DiHOME)。在oxy-18下的实验表明，7,10-DiHOME含有空气中的氧，并且由(10S)-HPOME通过异构化顺序形成。 (10R)-HPOME 未异构化。 (10S)-双加氧酶和氢过氧化物异构酶活性在离子交换色谱和凝胶过滤上共洗脱，表观分子大小约为 50 kDa。 16:1n-7、18:2n-6和20:1n-11也被氧化成7,10-二羟基脂肪酸，(8Z)-18:1被氧化成6,9-二羟基-(7E) -十八碳烯酸。一系列双键位置更靠近（(6Z)-18:1、(5Z,9Z)-18:2）或更远离羧基的脂肪酸（(11Z)-、(13Z)-和(15Z)-18:1) 是较差的