Octadecanoic acid 2-[hydroxy-(8-hydroxy-octyloxy)-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester | 167013-40-3

• 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: Octadecanoic acid 2-[hydroxy-(8-hydroxy-octyloxy)-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester
• 英文别名: [3-[Hydroxy(8-hydroxyoctoxy)phosphoryl]oxy-2-octadecanoyloxypropyl] octadecanoate
• CAS: 167013-40-3
• 化学式: C₄₇H₉₃O₉P
• 分子量: 833.224
• InChiKey: GTFGURYCXGHEJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.5
• 重原子数：
  57
• 可旋转键数：
  49
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Octadecanoic acid 2-[hydroxy-(8-hydroxy-octyloxy)-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester 在 palladium on activated charcoal 盐酸 、 disodium hydrogenphosphate 、 4 A molecular sieve 、 potassium methanolate 、 氢气 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 乙醇 、 氯仿 、 甲苯 为溶剂， 35.0 ℃ 、101.33 kPa 条件下， 反应 25.0h， 生成 (2R,4S,5R,6R)-5-Acetylamino-2-{8-[(2,3-bis-octadecanoyloxy-propoxy)-hydroxy-phosphoryloxy]-octyloxy}-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of a Novel Sialic Acid Derivative (Sialylphospholipid) as an Antirotaviral Agent

  摘要：

  A novel sialylphospholipid (SPL) was synthesized from N-acetylneuraminic acid (NeuAc) and phosphatidylcholine (PC) by a chemical and enzymatic method and evaluated as an inhibitor of rotavirus. PC and 1,8-octanediol were conjugated by transesterification reaction of Streptomyces phospholipase D (PLD) under a water-chloroform biphasic system to afford phosphatidyloctanol, which was condensed with a protected 2-chloro-2-deoxyneuraminic acid derivative by using silver trifluoromethanesulfonate as an activator in chloroform and converted, after deprotection, to SPL. Rhesus monkey kidney cells (MA-104) were incubated with simian (SA-11 strain) and human (MO strain) rotaviruses in the presence of SPL, and the cells infected were detected indirectly with anti-rotavirus antibody. SPL showed dose dependent inhibition against both virus strains. The concentrations required for 50% inhibition (IC50) against SA-11 and MO were 4.35 and 16.1 mu M, respectively, corresponding to 10(3)- and 10(4)-fold increases in inhibition as compared to monomeric NeuAc.

  DOI：

  10.1021/jm9701280
• 作为产物：
  描述：

  1,8-辛二醇 、 氢化磷脂酰胆碱 在 NaOAc buffer 、 Streptomyces phospholipase D 、 calcium acetate 作用下， 以 氯仿 为溶剂， 反应 50.0h， 以67.8%的产率得到Octadecanoic acid 2-[hydroxy-(8-hydroxy-octyloxy)-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester
  参考文献：
  名称：

  Synthesis of a Novel Sialic Acid Derivative (Sialylphospholipid) as an Antirotaviral Agent

  摘要：

  A novel sialylphospholipid (SPL) was synthesized from N-acetylneuraminic acid (NeuAc) and phosphatidylcholine (PC) by a chemical and enzymatic method and evaluated as an inhibitor of rotavirus. PC and 1,8-octanediol were conjugated by transesterification reaction of Streptomyces phospholipase D (PLD) under a water-chloroform biphasic system to afford phosphatidyloctanol, which was condensed with a protected 2-chloro-2-deoxyneuraminic acid derivative by using silver trifluoromethanesulfonate as an activator in chloroform and converted, after deprotection, to SPL. Rhesus monkey kidney cells (MA-104) were incubated with simian (SA-11 strain) and human (MO strain) rotaviruses in the presence of SPL, and the cells infected were detected indirectly with anti-rotavirus antibody. SPL showed dose dependent inhibition against both virus strains. The concentrations required for 50% inhibition (IC50) against SA-11 and MO were 4.35 and 16.1 mu M, respectively, corresponding to 10(3)- and 10(4)-fold increases in inhibition as compared to monomeric NeuAc.

  DOI：

  10.1021/jm9701280