Methyl 12-[(methanesulfonyl)oxy]dodecanoate | 110544-75-7

• 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: Methyl 12-[(methanesulfonyl)oxy]dodecanoate
• 英文别名: methyl 12-methylsulfonyloxydodecanoate
• CAS: 110544-75-7
• 化学式: C₁₄H₂₈O₅S
• 分子量: 308.439
• InChiKey: RIQRKTDBMZJFRP-UHFFFAOYSA-N

物化性质

• 沸点：
  415.0±18.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 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：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 12-[(methanesulfonyl)oxy]dodecanoate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 methyl 12-azidododecanoate
  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
• 作为产物：
  描述：

  12-羟基十二酸 在 三乙胺 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 Methyl 12-[(methanesulfonyl)oxy]dodecanoate
  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

• Combinatorial synthesis of PEG oligomer libraries
  申请人：Riggs-Sauthier A. Jennifer

  公开号：US20060008850A1

  公开（公告）日：2006-01-12

  A simple chain-extending approach was established for the scale-up of the monoprotected monodisperse PEG diol materials. Reactions of THP-(OCH 2 CH 2 ) n —OMs (n=4, 8, 12) with a large excess of commercially available H—(OCH 2 CH 2 ) n —OH (n=1-4) under basic conditions led to THP-(OCH 2 CH 2 ) n —OH (n=5-15). Similarly, Me-(OCH 2 CH 2 ) n —OH (n=4-11, 13) were prepared from Me-(OCH 2 CH 2 ) n —OMs (n=3, 7, 11). For the chain elongation steps, 40-80% yields were achieved through extraction purification. PEG oligomer libraries I and II were generated in 50-95% overall yields by alkylation or acylation of THP-(OCH 2 CH 2 ) n —OH (n=1-15) followed by deprotection. Alkylation of Me-(OCH 2 CH 2 ) n —OH (n=1-11, 13) with X—(CH 2 ) m —CO 2 R (X=Br or OMs) and subsequent hydrolysis led to PEG oligomer library III in 30-60% overall yields. Combinatorial purification techniques were adapted to the larger-scale library synthesis. A total of 498 compounds, each with a weight of 2-5 g and a minimum purity of 90%, were synthesized.

  建立了一种简单的链延伸方法，用于扩大单保护单分散PEG二醇材料的规模。在碱性条件下，THP-(OCH2CH2)n—OMs (n=4, 8, 12) 与大量商业可获得的H—(OCH2CH2)n—OH (n=1-4) 反应，形成THP-(OCH2CH2)n—OH (n=5-15)。类似地，Me-(OCH2CH2)n—OH (n=4-11, 13) 是由Me-(OCH2CH2)n—OMs (n=3, 7, 11) 制备而成的。对于链延伸步骤，通过提取纯化实现了40-80%的产率。通过烷基化或酰化THP-(OCH2CH2)n—OH (n=1-15) 后脱保护，生成了50-95%的总产率的PEG寡聚体库I和II。Me-(OCH2CH2)n—OH (n=1-11, 13) 与X—(CH2)m—CO2R (X=Br或OMs) 反应，随后水解，形成了30-60%的总产率的PEG寡聚体库III。组合纯化技术被应用于大规模库合成。共合成了498种化合物，每种重量为2-5克，最低纯度为90%。
• 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.