二(羟甲基)丙二酸二乙酯 | 130034-47-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 二(羟甲基)丙二酸二乙酯
• 英文名称: diethyl bis(hydroxymethyl)malonate
• 英文别名: Diethyl 3,3-bis(hydroxymethyl)pentanedioate
• CAS: 130034-47-8
• 化学式: C₁₁H₂₀O₆
• 分子量: 248.276
• InChiKey: DEIQMRKGTJJDNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二(羟甲基)丙二酸二乙酯 在 氢溴酸 作用下， 反应 6.0h， 以47%的产率得到3-溴-2-溴甲基丙酸
  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：

  聚合甲醛 、 丙二酸二乙酯 在 potassium carbonate 作用下， 以78%的产率得到二(羟甲基)丙二酸二乙酯
  参考文献：
  名称：

  Baker, Raymond; Boyes, Alastairs L.; Swain, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1990, # 5, p. 1415 - 1421

  摘要：

  DOI：

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.
• Baker, Raymond; Boyes, Alastairs L.; Swain, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1990, # 5, p. 1415 - 1421
  作者：Baker, Raymond、Boyes, Alastairs L.、Swain, Christopher J.

  DOI：——

  日期：——