3-hexadecylsulfanyl-2-hexadecylsulfanylmethyl-propionic acid 2-[2-(2-{2-[2-(2-methanesulfonyloxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethyl ester | 1092478-75-5

• 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: 3-hexadecylsulfanyl-2-hexadecylsulfanylmethyl-propionic acid 2-[2-(2-{2-[2-(2-methanesulfonyloxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethyl ester
• CAS: 1092478-75-5
• 化学式: C₄₉H₉₈O₁₀S₃
• 分子量: 943.509
• InChiKey: XMRWLJUIMLGCSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.63
• 重原子数：
  62.0
• 可旋转键数：
  54.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  115.82
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3-hexadecylsulfanyl-2-hexadecylsulfanylmethyl-propionic acid 2-[2-(2-{2-[2-(2-methanesulfonyloxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethyl ester 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 22.0h， 以90%的产率得到3-hexadecylsulfanyl-2-hexadecylsulfanylmethyl-propionic acid 2-[2-(2-{2-[2-(2-iodoethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethyl ester
  参考文献：
  名称：

  Efficient Synthesis of Methanesulphonate-Derived Lipid Chains for Attachment of Proteins to Lipid Membranes

  摘要：

  We have developed an easy and flexible synthetic methodology to obtain lipid chains containing methanothiosulfonate terminal groups with the aim to attach them to natural proteins as functional groups. There are many proteins found in nature that are modified by lipids, and this is a key part of their function. For example, the prion protein is attached to the plasma membrane via a glycosylphosphatidylinositol (GPI) anchor, and this protein is thought to be the causative agent in diseases such as bovine spongiform encephalopathy (BSE; mad cow disease) and the human equivalent Creutzfeldt-Jakob disease. However, production of large amounts of protein in bacteria results in proteins that lack these lipid modifications. The lipid chains containing methanothiosulfonate terminal groups that we have synthesized here can be attached to these proteins through the thiol contained in the side chain of the cysteine residue, which can be incorporated into the protein sequence at the desired position.

  DOI：

  10.1080/00397910802213794
• 作为产物：
  描述：

  3-hexadecylsulfanyl-2-hexadecylsulfanyl-propionic acid 2-[2-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethyl ester 、 甲基磺酰氯 在 吡啶 作用下， 以100%的产率得到3-hexadecylsulfanyl-2-hexadecylsulfanylmethyl-propionic acid 2-[2-(2-{2-[2-(2-methanesulfonyloxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethyl ester
  参考文献：
  名称：

  Efficient Synthesis of Methanesulphonate-Derived Lipid Chains for Attachment of Proteins to Lipid Membranes

  摘要：

  We have developed an easy and flexible synthetic methodology to obtain lipid chains containing methanothiosulfonate terminal groups with the aim to attach them to natural proteins as functional groups. There are many proteins found in nature that are modified by lipids, and this is a key part of their function. For example, the prion protein is attached to the plasma membrane via a glycosylphosphatidylinositol (GPI) anchor, and this protein is thought to be the causative agent in diseases such as bovine spongiform encephalopathy (BSE; mad cow disease) and the human equivalent Creutzfeldt-Jakob disease. However, production of large amounts of protein in bacteria results in proteins that lack these lipid modifications. The lipid chains containing methanothiosulfonate terminal groups that we have synthesized here can be attached to these proteins through the thiol contained in the side chain of the cysteine residue, which can be incorporated into the protein sequence at the desired position.

  DOI：

  10.1080/00397910802213794