3-hexadecylsulfanyl-2-hexadecylsulfanylmethyl-propionic acid 2-{2-[2-(2-{2-[2-(tert-butyldimethylsilanyloxy)ethoxy]ethoxy}ethoxy)ethoxy]ethoxy}ethyl ester | 1092478-70-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-hexadecylsulfanyl-2-hexadecylsulfanylmethyl-propionic acid 2-{2-[2-(2-{2-[2-(tert-butyldimethylsilanyloxy)ethoxy]ethoxy}ethoxy)ethoxy]ethoxy}ethyl ester
• 英文别名: 2-[2-[2-[2-[2-[2-[Tert-butyl(dimethyl)silyl]oxyethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 3-hexadecylsulfanyl-2-(hexadecylsulfanylmethyl)propanoate；2-[2-[2-[2-[2-[2-[tert-butyl(dimethyl)silyl]oxyethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 3-hexadecylsulfanyl-2-(hexadecylsulfanylmethyl)propanoate
• CAS: 1092478-70-0
• 化学式: C₅₄H₁₁₀O₈S₂Si
• 分子量: 979.68
• InChiKey: PCSWLVSPCGOJQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.68
• 重原子数：
  65
• 可旋转键数：
  56
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-hexadecylsulfanyl-2-hexadecylsulfanylmethyl-propionic acid 2-{2-[2-(2-{2-[2-(tert-butyldimethylsilanyloxy)ethoxy]ethoxy}ethoxy)ethoxy]ethoxy}ethyl ester 在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.33h， 以100%的产率得到3-hexadecylsulfanyl-2-hexadecylsulfanyl-propionic acid 2-[2-(2-{2-[2-(2-hydroxyethoxy)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-hexadecylsulfanylmethylpropionic acid 、 TBDMS-六聚乙二醇-羟基 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以76%的产率得到3-hexadecylsulfanyl-2-hexadecylsulfanylmethyl-propionic acid 2-{2-[2-(2-{2-[2-(tert-butyldimethylsilanyloxy)ethoxy]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

文献信息

• Efficient Synthesis of Methanesulphonate-Derived Lipid Chains for Attachment of Proteins to Lipid Membranes
  作者：Matthew R. Hicks、Atvinder K. Rullay、Rosa Pedrido、David H. Crout、Teresa J. T. Pinheiro

  DOI：10.1080/00397910802213794

  日期：2008.10.22

  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.