(1-benzo[1,2,5]oxadiazol-5-ylmethyl-1H-[1,2,3]triazol-4-ylmethyl)-{2-[(2-hexadecanoylamino-3-hydroxyoctadec-4-enyloxy)hydroxyphosphoryloxy]ethyl}dimethylammonium | 1196670-49-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (1-benzo[1,2,5]oxadiazol-5-ylmethyl-1H-[1,2,3]triazol-4-ylmethyl)-{2-[(2-hexadecanoylamino-3-hydroxyoctadec-4-enyloxy)hydroxyphosphoryloxy]ethyl}dimethylammonium
• 英文别名: 2-[[1-(2,1,3-benzoxadiazol-5-ylmethyl)triazol-4-yl]methyl-dimethylazaniumyl]ethyl [(E,2S,3R)-2-(hexadecanoylamino)-3-hydroxyoctadec-4-enyl] phosphate
• CAS: 1196670-49-1
• 化学式: C₄₈H₈₄N₇O₇P
• 分子量: 902.211
• InChiKey: XPFILYFKQPVNHB-SNRBZAAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  63
• 可旋转键数：
  40
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  178
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  5-(azidomethyl)benzo[c][1,2,5]oxadiazole 、 {2-[(2-hexadecanoylamino-3-hydroxyoctadec-4-enyloxy)hydroxyphosphoryloxy]ethyl}dimethylprop-2-ynylammonium 在 copper(II) sulfate 、 维生素 C 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以100%的产率得到(1-benzo[1,2,5]oxadiazol-5-ylmethyl-1H-[1,2,3]triazol-4-ylmethyl)-{2-[(2-hexadecanoylamino-3-hydroxyoctadec-4-enyloxy)hydroxyphosphoryloxy]ethyl}dimethylammonium
  参考文献：
  名称：

  A Modular Synthesis of Alkynyl-Phosphocholine Headgroups for Labeling Sphingomyelin and Phosphatidylcholine

  摘要：

  A general route to phospho- and sphingolipids that incorporate an alkyne in the phosphocholine headgroup is described. The strategy preserves the ammonium functionality of the phosphocholine and call be easily modified to introduce desired functional groups at the N-acyl chain. The targets accessible with this strategy provide a bioorthogonal handle for postsynthetic introduction of fluorophores or other labeling agents with aqueous phase chemistry. We report the synthesis of sphingomyelin derivatives that incorporate a fluorophore and an alkyne. The modified sphingolipids retain activity as substrates for sphingomyelinase, making these compounds viable probes of enzymatic activity. Importantly, the strategy allows modification of the lipid across the phosphodiester, making the alkyne a potential probe of sphingomyelinase activity.

  DOI：

  10.1021/jo901824h

文献信息

• A Modular Synthesis of Alkynyl-Phosphocholine Headgroups for Labeling Sphingomyelin and Phosphatidylcholine
  作者：Mahendra S. Sandbhor、Jessie A. Key、Ileana S. Strelkov、Christopher W. Cairo

  DOI：10.1021/jo901824h

  日期：2009.11.20

  A general route to phospho- and sphingolipids that incorporate an alkyne in the phosphocholine headgroup is described. The strategy preserves the ammonium functionality of the phosphocholine and call be easily modified to introduce desired functional groups at the N-acyl chain. The targets accessible with this strategy provide a bioorthogonal handle for postsynthetic introduction of fluorophores or other labeling agents with aqueous phase chemistry. We report the synthesis of sphingomyelin derivatives that incorporate a fluorophore and an alkyne. The modified sphingolipids retain activity as substrates for sphingomyelinase, making these compounds viable probes of enzymatic activity. Importantly, the strategy allows modification of the lipid across the phosphodiester, making the alkyne a potential probe of sphingomyelinase activity.