ω-azido-tetradecanoic acid | 176108-61-5

• 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: ω-azido-tetradecanoic acid
• 英文别名: 14-Azido-tetradecanoic acid；14-azidotetradecanoic acid
• CAS: 176108-61-5
• 化学式: C₁₄H₂₇N₃O₂
• 分子量: 269.387
• InChiKey: BDKKINJEPJYWSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  51.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  14-羟基豆蔻酸 在 sodium hydroxide 、 sodium azide 、 三乙胺 、 乙酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 ω-azido-tetradecanoic acid
  参考文献：
  名称：

  Chemical Probes for the Rapid Detection of Fatty-Acylated Proteins in Mammalian Cells

  摘要：

  The attachment of lipids onto proteins modulates the activity of proteins in many biological settings. The analysis of protein lipidation, however, is challenging due to the relatively few methods for the detection of lipid-modified proteins. Here we describe the synthesis of omega-azido-fatty acids as non-radioactive chemical probes for the rapid visualization of fatty-acylated proteins in mammalian cells. Following metabolic installation of the omega-azido-fatty acids onto target proteins by cellular enzymes, fatty-acylated proteins are selectively biotinylated with a phosphine-biotin reagent via the Staudinger ligation and visualized by streptavidin blotting. Depending on the chain length of the omega-azido-fatty acids, N-myristoylated and S-palmitoylated proteins can be visualized selectively in cell lysates and on specific proteins. These chemical probes provide new tools to analyze fatty acylation of proteins in living cells.

  DOI：

  10.1021/ja0685001

文献信息

• Anti-viral azide containing compounds
  申请人：LIFE TECHNOLOGIES CORPORATION

  公开号：US10179143B2

  公开（公告）日：2019-01-15

  Methods of using azide-modified biomolecules, such as fatty acids, carbohydrates and lipids, to treat a plant, an insect or an animal infected with a virus or to inhibit infectivity of a virus, such as the human immunodeficiency virus, are provided. Also provided are methods of labeling a virus, such as human immunodeficiency virus, with an azide-modified biomolecule, such as a fatty acid, a carbohydrate, or an isoprenoid lipid. Also, provided are methods of tracking a virus in vivo, with an azide-modified biomolecule, such as a fatty acid, a carbohydrate, or an isoprenoid lipid. The azide-modified biomolecules may be combined with a pharmaceutically acceptable excipient to produce a pharmaceutical composition, optionally containing another anti-viral agent and/or a delivery agent, such as a liposome.

  提供了使用叠氮修饰的生物大分子（如脂肪酸、碳水化合物和脂质）治疗感染病毒的植物、昆虫或动物或抑制病毒（如人类免疫缺陷病毒）感染性的方法。还提供了用叠氮修饰的生物大分子（如脂肪酸、碳水化合物或异戊烯类脂质）标记病毒（如人类免疫缺陷病毒）的方法。此外，还提供了利用叠氮修饰的生物大分子（如脂肪酸、碳水化合物或异戊烯类脂质）在体内追踪病毒的方法。叠氮修饰的生物大分子可与药学上可接受的赋形剂结合，制成药物组合物，其中可选择含有另一种抗病毒剂和/或递送剂，如脂质体。
• Chemical Probes for the Rapid Detection of Fatty-Acylated Proteins in Mammalian Cells
  作者：Howard C. Hang、Ernst-Jan Geutjes、Gijsbert Grotenbreg、Annette M. Pollington、Marie Jose Bijlmakers、Hidde L. Ploegh

  DOI：10.1021/ja0685001

  日期：2007.3.1

  The attachment of lipids onto proteins modulates the activity of proteins in many biological settings. The analysis of protein lipidation, however, is challenging due to the relatively few methods for the detection of lipid-modified proteins. Here we describe the synthesis of omega-azido-fatty acids as non-radioactive chemical probes for the rapid visualization of fatty-acylated proteins in mammalian cells. Following metabolic installation of the omega-azido-fatty acids onto target proteins by cellular enzymes, fatty-acylated proteins are selectively biotinylated with a phosphine-biotin reagent via the Staudinger ligation and visualized by streptavidin blotting. Depending on the chain length of the omega-azido-fatty acids, N-myristoylated and S-palmitoylated proteins can be visualized selectively in cell lysates and on specific proteins. These chemical probes provide new tools to analyze fatty acylation of proteins in living cells.