2-bromooctadec-17-ynoic acid | 1431947-87-3

• 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: 2-bromooctadec-17-ynoic acid
• CAS: 1431947-87-3
• 化学式: C₁₈H₃₁BrO₂
• 分子量: 359.347
• InChiKey: JIVFVUDHJOJMGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-bromooctadec-17-ynal 在 重铬酸吡啶 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-bromooctadec-17-ynoic acid
  参考文献：
  名称：

  2-Bromopalmitate Analogues as Activity-Based Probes To Explore Palmitoyl Acyltransferases

  摘要：

  Reversible S-palmitoylation is an important post-translational modification that regulates the trafficking, localization, and activity of proteins. Cysteine-rich Asp-His-His-Cys (DHHC) domain-containing enzymes are evolutionarily conserved protein palmitoyl acyltransferases (PATs). The human genome encodes 23 DHHC-PATs that regulate diverse cellular functions. Although chemical probes and proteomic methods to detect palmitoylated protein substrates have been reported, no probes for direct detection of the activity of PATs are available. Here we report the synthesis and characterization of 2-bromohexadec-15-ynoic acid and 2-bromooctadec-17-ynoic acid, which are analogues of 2-bromopalmitate (2-BP), as activity-based probes for PATs as well as other palmitoylating and 2-BP-binding enzymes. These probes will serve as new chemical tools for activity-based protein profiling to explore PATs, to dissect the functions of PATs in cell signaling and diseases, and to facilitate the identification of their inhibitors.

  DOI：

  10.1021/ja311416v