10-羟基十四烷酸 | 16899-08-4

• 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: 10-羟基十四烷酸
• 英文名称: 10-hydroxytetradecanoic acid
• 英文别名: 10-hydroxy-tetradecanoic acid；10-Hydroxy-tetradecansaeure；10-Hydroxy-myristinsaeure；10-Hydroxytetradecansaeure
• CAS: 16899-08-4
• 化学式: C₁₄H₂₈O₃
• 分子量: 244.375
• InChiKey: WWQJYRLZAYKMGV-UHFFFAOYSA-N

物化性质

• 熔点：
  56-57 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• 沸点：
  381.7±15.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  10-羟基十四烷酸 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 10-氧代十四酸
  参考文献：
  名称：

  REDUCTIONS WITH NICKEL-ALUMINUM ALLOY AND AQUEOUS ALKALI. PART VII. HYDROGENOLYSIS OF SULFUR COMPOUNDS¹

  摘要：

  DOI：

  10.1021/jo01157a002
• 作为产物：
  描述：

  肉豆蔻油酸 在 oleate hydratase from macrococcus caseolyticus 、 水 、 腺嘌呤黄素 作用下， 以 乙醇 为溶剂， 反应 0.17h， 生成 10-羟基十四烷酸
  参考文献：
  名称：

  Biochemical characterization and FAD-binding analysis of oleate hydratase from Macrococcus caseolyticus

  摘要：

  A putative fatty acid hydratase gene from Macrococcus caseolyticus was cloned and expressed in Escherichia coli. The recombinant enzyme was a 68 kDa dimer with a molecular mass of 136 kDa. The enzyrnatic products formed from fatty acid substrates by the putative enzyme were isolated with high purity (>99%) by solvent fractional crystallization at low temperature. After the identification by GC MS, the purified hydroxy fatty acids were used as standards to quantitatively determine specific activities and kinetic parameters for fatty acids as substrates. Among the fatty acids evaluated, specific activity and catalytic efficiency (k t1Kin) were highest for oleic acid, indicating that the putative fatty acid hydratase was an oleate hydratase. Hydration occurred only for cis-9-double and cis-12-double bonds of unsaturated fatty acids without any trans-configurations. The maximum activity for oleate hydration was observed at pH 6.5 and 25 C with 2% (v/v) ethanol and 0.2 mM FAD. Without FAD, all catalytic activity was abolished. Thus, the oleate hydratase is an FAD-dependent enzyme. The residues G29, G31, S34, E50, and E56, which are conserved in the FAD-binding motif of fatty acid hydratases (GXGXXG((A/S))X((15-21))E(D), were selected by alignment, and the spectral properties and kinetic parameters of their alanine-substituted variants were analyzed. Among the five variants, G29A. G31A, and E56A showed no interaction with FAD and exhibited no activity. These results indicate that G29, G31, and E56 are essential for FAD-binding. Crown Copyright (C) 2011 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2011.12.011

文献信息

• Controlling Chemoselectivity of Catalytic Hydroboration with Light
  作者：Enrico Bergamaschi、Danijela Lunic、Liam A. McLean、Melissa Hohenadel、Yi‐Kai Chen、Christopher J. Teskey

  DOI：10.1002/anie.202114482

  日期：2022.2.14

  Light-controllable, chemoselective hydroboration of ketoacids is reported using a well-defined cobalt hydride catalyst. Excellent selectivities can be achieved, with acids reacting in the dark and ketones in the light. This approach can be further extended to other functional groups.

  据报道，使用明确的氢化钴催化剂对酮酸进行光控、化学选择性硼氢化。可以实现优异的选择性，酸在黑暗中反应，酮在光下反应。这种方法可以进一步扩展到其他功能组。
• [EN] DRUG CONJUGATES<br/>[FR] CONJUGUÉS DE MÉDICAMENT
  申请人：UNIV MISSOURI

  公开号：WO2009158633A1

  公开（公告）日：2009-12-30

  Conjugated compounds comprising a therapeutic or diagnostic agent linked to a substrate for a cell membrane transporter or receptor by lipophilic linker are provided.

  提供了包含治疗或诊断药物与细胞膜转运体或受体的底物通过亲脂性连接剂连接的共轭化合物。
• The CYPome of Sorangium cellulosum So ce56 and Identification of CYP109D1 as a New Fatty Acid Hydroxylase
  作者：Yogan Khatri、Frank Hannemann、Kerstin M. Ewen、Dominik Pistorius、Olena Perlova、Norio Kagawa、Alexander O. Brachmann、Rolf Müller、Rita Bernhardt

  DOI：10.1016/j.chembiol.2010.10.010

  日期：2010.12

  studies on the characterization of fatty acid hydroxylases. Three novel potential fatty acid hydroxylases (CYP109D1, CYP264A1, and CYP266A1) were used for detailed characterization. One of them, CYP109D1 was able to perform subterminal hydroxylation of saturated fatty acids with the support of two autologous and one heterologous electron transfer system(s). The kinetic parameters for the product hydroxylation

  提出了对纤维素酶Soce56的完整细胞色素P450补体（CYPome）进行的首次系统研究，该酶是重要的次生代谢产物的生产者，具有迄今为止最大的细菌基因组序列。我们描述了由21个推定的P450基因组成的Soce56细胞色素P450补体的生物信息学分析。由于脂肪酸在黏菌的复杂生命周期中起着关键作用，因此我们将研究重点放在了脂肪酸羟化酶的表征上。三种新颖的潜在脂肪酸羟化酶（CYP109D1，CYP264A1和CYP266A1）用于详细表征。其中之一，CYP109D1能够在两个自体和一个异源电子转移系统的支持下进行饱和脂肪酸的亚末端羟基化反应。
• Selective carbon-hydrogen bond hydroxylation using an engineered cytochrome P450 peroxygenase
  作者：Jinia Akter、Tegan P. Stockdale、Stella A. Child、Joel H.Z. Lee、James J. De Voss、Stephen G. Bell

  DOI：10.1016/j.jinorgbio.2023.112209

  日期：2023.7

  linear fatty acids tested (undecanoic through to hexadecenoic acid) when compared to the wild-type heme domain. The product distributions arising from fatty acid oxidation using this peroxygenase variant were broadly similar to those obtained with the wild-type monooxygenase holoenzyme, with oxidation occurring predominantly at the ω-1 through to ω-3 positions. 10-Undecenoic acid was regioselectively

  细胞色素 P450酶 CYP102A1 (P450BM3) 是一种多功能单加氧酶，已针对化学合成中的多种应用进行了改造和设计。苏氨酸 268 突变为谷氨酸 (Thr268Glu)，利用过氧酶将该酶的血红素结构域转化为 H 2O2。与野生型血红素结构域相比，该变体对所测试的饱和直链脂肪酸（十一碳烯酸至十六碳烯酸）表现出显着增加的过氧化物驱动的羟基化活性。脂肪酸产生的产品分布使用这种过氧化酶变体的氧化与使用野生型单加氧酶全酶获得的氧化大致相似，氧化主要发生在 ω-1 至 ω-3 位点。Thr268Glu 过氧化酶将 10-十一碳烯酸在烯丙基 ω-2 碳上进行区域选择性羟基化。使用[9,9,10,10- d 4 ]-十二烷酸测量同位素取代的效果。单加氧酶和过氧合酶系统的动力学同位素效应范围在 7.9 和 9.5 之间，过氧合酶的动力学同位素效应略低。这凸显了碳氢键抽象在单加氧酶和过加氧酶系统的机制中都很重要。这可以推断
• Efficient biocatalytic C–H bond oxidation: an engineered heme-thiolate peroxygenase from a thermostable cytochrome P450
  作者：Alecia R. Gee、Isobella S. J. Stone、Tegan P. Stockdale、Tara L. Pukala、James J. De Voss、Stephen G. Bell

  DOI：10.1039/d3cc04626e

  日期：——

  highly sought after reaction in chemical synthesis is the activation of unactivated carbon–hydrogen bonds. We demonstrate the hydroxylation of fatty acids using an engineered thermostable archaeal cytochrome P450 enzyme. By replacing a seven amino acid section of the I-helix, the nicotinamide cofactor-dependent monooxygenase was converted into a hydrogen peroxide using peroxygenase, enabling the efficient

  化学合成中备受追捧的反应是未活化的碳氢键的活化。我们使用工程化的热稳定古菌细胞色素 P450 酶演示了脂肪酸的羟基化。通过替换 I 螺旋的 7 个氨基酸部分，烟酰胺辅因子依赖性单加氧酶使用过加氧酶转化为过氧化氢，从而能够在室温至 90 °C 下对 C-H 键进行有效的生物催化氧化。