1-O-palmitoyl-2-O-(12-acryloyloxy)dodecanoyl-sn-glycero-3-phosphoethanolamine | 370102-89-9

• 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: 1-O-palmitoyl-2-O-(12-acryloyloxy)dodecanoyl-sn-glycero-3-phosphoethanolamine
• 英文别名: [(2R)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-(12-prop-2-enoyloxydodecanoyloxy)propyl] hexadecanoate
• CAS: 370102-89-9
• 化学式: C₃₆H₆₈NO₁₀P
• 分子量: 705.91
• InChiKey: OJJZXHLIYVMGPG-MGBGTMOVSA-N

物化性质

• 沸点：
  737.1±70.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  48
• 可旋转键数：
  39
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  161
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (+)生物素-N-琥珀酰亚胺基酯 、 1-O-palmitoyl-2-O-(12-acryloyloxy)dodecanoyl-sn-glycero-3-phosphoethanolamine 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以53%的产率得到
  参考文献：
  名称：

  A facile synthesis of bifunctional phospholipids for biomimetic membrane engineering

  摘要：

  We report a facile synthesis of bifunctional phospholipid conjugates by acylation of N-protected lyso-phosphatidylethanolamine with 12-acryloxy-1-dodecanoic acid and followed with deprotection and conjugation with biotin, FITC, Texas Red, or EMC groups. The lipid conjugates can be used to generate a multifunctional substrate-supported phospholipid membrane via bioconjugation reaction to biotin or covalent attachment to EMC at their hydrophilic terminus. In addition, conjugation to fluorophores, FITC or Texas Red, provides a convenient mechanism to monitor lipid membrane formation and stability. Significantly, in situ photopolymerization of the acrylate group at the end of one of two hydrophobic alkyl chains stabilizes the phospholipid membrane. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.110
• 作为产物：
  描述：

  12-羟基十二酸 在 吡啶 、 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基苯酚 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 68.0h， 生成 1-O-palmitoyl-2-O-(12-acryloyloxy)dodecanoyl-sn-glycero-3-phosphoethanolamine
  参考文献：
  名称：

  A facile synthesis of bifunctional phospholipids for biomimetic membrane engineering

  摘要：

  We report a facile synthesis of bifunctional phospholipid conjugates by acylation of N-protected lyso-phosphatidylethanolamine with 12-acryloxy-1-dodecanoic acid and followed with deprotection and conjugation with biotin, FITC, Texas Red, or EMC groups. The lipid conjugates can be used to generate a multifunctional substrate-supported phospholipid membrane via bioconjugation reaction to biotin or covalent attachment to EMC at their hydrophilic terminus. In addition, conjugation to fluorophores, FITC or Texas Red, provides a convenient mechanism to monitor lipid membrane formation and stability. Significantly, in situ photopolymerization of the acrylate group at the end of one of two hydrophobic alkyl chains stabilizes the phospholipid membrane. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.110

文献信息

• Antithrombogenic membrane mimetic compositions and methods
  申请人：——

  公开号：US20040073295A1

  公开（公告）日：2004-04-15

  The present Specification describes materials and methods which provide for improved performance of medical prostheses, including vascular graft material, artificial heart valves, and other implanted materials. The materials comprising bound thrombomodulin or a functionally equivalent derivative protein, provide for fewer undesirable side effects including inflammation, thromboses and neointimal hyperplasia.

  本说明书描述的材料和方法可改善医疗假体的性能，包括血管移植材料、人工心脏瓣膜和其他植入材料。包含结合血栓调节蛋白或功能相当的衍生物蛋白的材料可减少不良副作用，包括炎症、血栓形成和新内膜增生。
• US6936298B2
  申请人：——

  公开号：US6936298B2

  公开（公告）日：2005-08-30
• A facile synthesis of bifunctional phospholipids for biomimetic membrane engineering
  作者：Xue-Long Sun、Wanxing Cui、Toshistugu Kai、Elliot L. Chaikof

  DOI：10.1016/j.tet.2004.09.110

  日期：2004.12

  We report a facile synthesis of bifunctional phospholipid conjugates by acylation of N-protected lyso-phosphatidylethanolamine with 12-acryloxy-1-dodecanoic acid and followed with deprotection and conjugation with biotin, FITC, Texas Red, or EMC groups. The lipid conjugates can be used to generate a multifunctional substrate-supported phospholipid membrane via bioconjugation reaction to biotin or covalent attachment to EMC at their hydrophilic terminus. In addition, conjugation to fluorophores, FITC or Texas Red, provides a convenient mechanism to monitor lipid membrane formation and stability. Significantly, in situ photopolymerization of the acrylate group at the end of one of two hydrophobic alkyl chains stabilizes the phospholipid membrane. (C) 2004 Elsevier Ltd. All rights reserved.