2-bromohexadec-15-ynoic acid | 1431947-86-2

• 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-bromohexadec-15-ynoic acid
• 英文别名: Alkynyl 2-Bromo-Palmitic Acid
• CAS: 1431947-86-2
• 化学式: C₁₆H₂₇BrO₂
• 分子量: 331.293
• InChiKey: CJLAGCHLAMRSPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  15-十六碳炔-1-醇 在 重铬酸吡啶 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 L-脯氨酸 、 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-bromohexadec-15-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

文献信息

• TEAD transcription factor autopalmitoylation inhibitors
  申请人：The General Hospital Corporation

  公开号：US10696642B2

  公开（公告）日：2020-06-30

  The present disclosure compounds, as well as their compositions and methods of use. The compounds inhibit the activity of the TEAD transcription factor, and are useful in the treatment of diseases related to the activity of TEAD transcription factor including, e.g., cancer and other diseases.

  本公开的化合物及其组合物和使用方法。这些化合物抑制 TEAD 转录因子的活性，可用于治疗与 TEAD 转录因子活性有关的疾病，包括癌症和其他疾病。
• TEAD TRANSCRIPTION FACTOR AUTOPALMITOYLATION INHIBITORS
  申请人：The General Hospital Corporation

  公开号：EP3353156A1

  公开（公告）日：2018-08-01
• [EN] TEAD TRANSCRIPTION FACTOR AUTOPALMITOYLATION INHIBITORS<br/>[FR] INHIBITEURS DE L'AUTOPALMITOYLATION DU FACTEUR DE TRANSCRIPTION TEAD
  申请人：MASSACHUSETTS GEN HOSPITAL

  公开号：WO2017053706A1

  公开（公告）日：2017-03-30

  The present disclosure compounds, as well as their compositions and methods of use. The compounds inhibit the activity of the TEAD transcription factor, and are useful in the treatment of diseases related to the activity of TEAD transcription factor including, e.g., cancer and other diseases.
• 2-Bromopalmitate Analogues as Activity-Based Probes To Explore Palmitoyl Acyltransferases
  作者：Baohui Zheng、Michael DeRan、Xinyan Li、Xuebin Liao、Masaki Fukata、Xu Wu

  DOI：10.1021/ja311416v

  日期：2013.5.15

  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.