O-<1-O-(11-Carboxyundecyl)-2-O-methyl-sn-glycero-3-phosphoryl>(p-nitrophenyl)ethanol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: O-<1-O-(11-Carboxyundecyl)-2-O-methyl-sn-glycero-3-phosphoryl>(p-nitrophenyl)ethanol
• 英文别名: O-[1-O-(11-Carboxyundecyl)-2-O-methyl-sn-glycero-3-phosphoryl](p-nitrophenyl)ethanol；12-[(2R)-3-[hydroxy-[2-(4-nitrophenyl)ethoxy]phosphoryl]oxy-2-methoxypropoxy]dodecanoic acid
• 化学式: C₂₄H₄₀NO₁₀P
• 分子量: 533.556
• InChiKey: CGJUBQQPJWVSIL-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  36
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  157
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  12-羟基十二酸 在 吡啶 、 盐酸 、 sodium hydroxide 、 三氟化硼乙醚 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 58.0h， 生成 O-<1-O-(11-Carboxyundecyl)-2-O-methyl-sn-glycero-3-phosphoryl>(p-nitrophenyl)ethanol
  参考文献：
  名称：

  A General Synthetic Route for Preparing Ether Phospholipids Suitable for Immobilization: A Phosphotriester Approach

  摘要：

  A synthetic route was developed to prepare ether phospholipid (PL) ligands suitable for immobilization. PL ligand design included an omega-carboxyl functional group to assure proper molecular orientation during immobilization; i.e., the polar lipid head group protrudes from the surface. However, during immobilization, PL ligands required protecting groups to eliminate the possibility of the PL binding upside down. Four synthetic PL ligands were prepared that contain both omega-carboxyl groups for immobilization and protecting groups in the polar head group; these carboxyl-PL ligands are analogs of phosphatidylethanolamine (PE), phosphatidylserine (PS), phosphatidylglycerol (PG), and phosphatidic acid (PA). The critical synthetic step during PL synthesis is the phosphorylation step which usually has the lowest yield of all other steps. This is the first report demonstrating that o-chlorophenyl dichloro phosphate (CPDCP) can be used as a mild phosphorylation reagent for the preparation of PL analogs. Phosphorylation with CPDCP is routinely 50-90 % efficient depending on the analog, but more important is that the protecting groups associated with PE, PS, PG, and PA are stable during this critical synthetic step. After immobilization of the carboxyl-PL ligands, acidic or basic solution conditions are needed for deprotection and generation of free PE, PG, PS, and PA polar lipid headgroups which protrude from the surface. This work demonstrates that CPDCP is an excellent synthetic reagent for all ether PL analogs either with or without omega-carboxyl functional groups.

  DOI：

  10.1021/jo00082a009

文献信息

• A General Synthetic Route for Preparing Ether Phospholipids Suitable for Immobilization: A Phosphotriester Approach
  作者：Xiaoxing Qiu、Shaowei Ong、Candido Bernal、Dongmi Rhee、Charles Pidgeon

  DOI：10.1021/jo00082a009

  日期：1994.2

  A synthetic route was developed to prepare ether phospholipid (PL) ligands suitable for immobilization. PL ligand design included an omega-carboxyl functional group to assure proper molecular orientation during immobilization; i.e., the polar lipid head group protrudes from the surface. However, during immobilization, PL ligands required protecting groups to eliminate the possibility of the PL binding upside down. Four synthetic PL ligands were prepared that contain both omega-carboxyl groups for immobilization and protecting groups in the polar head group; these carboxyl-PL ligands are analogs of phosphatidylethanolamine (PE), phosphatidylserine (PS), phosphatidylglycerol (PG), and phosphatidic acid (PA). The critical synthetic step during PL synthesis is the phosphorylation step which usually has the lowest yield of all other steps. This is the first report demonstrating that o-chlorophenyl dichloro phosphate (CPDCP) can be used as a mild phosphorylation reagent for the preparation of PL analogs. Phosphorylation with CPDCP is routinely 50-90 % efficient depending on the analog, but more important is that the protecting groups associated with PE, PS, PG, and PA are stable during this critical synthetic step. After immobilization of the carboxyl-PL ligands, acidic or basic solution conditions are needed for deprotection and generation of free PE, PG, PS, and PA polar lipid headgroups which protrude from the surface. This work demonstrates that CPDCP is an excellent synthetic reagent for all ether PL analogs either with or without omega-carboxyl functional groups.