(2R,14S,17S,23S,24R)-23-ammonio-14-((2-((carboxymethyl)-amino)-2-oxoethyl)carbamoyl)-24-hydroxy-17-((R)-1-hydroxyethyl)-9-methyl-4,16,19,22-tetraoxo-2-((palmitoyl-oxy)-methyl)-3-oxa-9,15,18,21-tetraazapentacosyl-(2-(trimethylammonio)ethyl)phosphate 2,2,2-trifluoroacetate | 1393646-47-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,14S,17S,23S,24R)-23-ammonio-14-((2-((carboxymethyl)-amino)-2-oxoethyl)carbamoyl)-24-hydroxy-17-((R)-1-hydroxyethyl)-9-methyl-4,16,19,22-tetraoxo-2-((palmitoyl-oxy)-methyl)-3-oxa-9,15,18,21-tetraazapentacosyl-(2-(trimethylammonio)ethyl)phosphate 2,2,2-trifluoroacetate
• 英文别名: [(2R)-2-[5-[[(5S)-5-[[(2S,3R)-2-[[2-[[(2S,3R)-2-amino-3-hydroxybutanoyl]amino]acetyl]amino]-3-hydroxybutanoyl]amino]-6-[[2-(carboxymethylamino)-2-oxoethyl]amino]-6-oxohexyl]-methylamino]pentanoyloxy]-3-hexadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate;2,2,2-trifluoroacetic acid
• CAS: 1393646-47-3
• 化学式: C₂HF₃O₂*C₅₀H₉₅N₈O₁₇P
• 分子量: 1225.35
• InChiKey: NCMOYVMRHCOLKI-GCTIRREOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  83
• 可旋转键数：
  49
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  401
• 氢给体数：
  10
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  1-乙酰基咪唑 、 (2R,14S,17S,23S,24R)-23-ammonio-14-((2-((carboxymethyl)-amino)-2-oxoethyl)carbamoyl)-24-hydroxy-17-((R)-1-hydroxyethyl)-9-methyl-4,16,19,22-tetraoxo-2-((palmitoyl-oxy)-methyl)-3-oxa-9,15,18,21-tetraazapentacosyl-(2-(trimethylammonio)ethyl)phosphate 2,2,2-trifluoroacetate 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以60%的产率得到(4S,10S,13S,25R)-13-((2-((carboxymethyl)amino)-2-oxoethyl)carbamoyl)-4,10-bis((R)-1-hydroxyethyl)-18-methyl-2,5,8,11,23-pentaoxo-25-((palmitoyloxy)methyl)-24-oxa-3,6,9,12,18-pentaazahexacosan-26-yl-(2-(trimethylammonio)-ethyl)phosphate
  参考文献：
  名称：

  Design and Synthesis of a Stable Oxidized Phospholipid Mimic with Specific Binding Recognition for Macrophage Scavenger Receptors

  摘要：

  Macrophage scavenger receptors appear to play a major role in the clearance of oxidized phospholipid (OxPL) products. Discrete peptide-phospholipid conjugates with the phosphatidylcholine headgroup have been shown to exhibit binding affinity for these receptors. We report the preparation of a water-soluble, stable peptide-phospholipid conjugate (9) that possesses the necessary physical properties to enable more detailed study of the role(s) of OxPL in metabolic disease.

  DOI：

  10.1021/jm300685s
• 作为产物：
  描述：

  溶血磷脂酰胆碱(鸡蛋) 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 4.5h， 生成 (2R,14S,17S,23S,24R)-23-ammonio-14-((2-((carboxymethyl)-amino)-2-oxoethyl)carbamoyl)-24-hydroxy-17-((R)-1-hydroxyethyl)-9-methyl-4,16,19,22-tetraoxo-2-((palmitoyl-oxy)-methyl)-3-oxa-9,15,18,21-tetraazapentacosyl-(2-(trimethylammonio)ethyl)phosphate 2,2,2-trifluoroacetate
  参考文献：
  名称：

  Design and Synthesis of a Stable Oxidized Phospholipid Mimic with Specific Binding Recognition for Macrophage Scavenger Receptors

  摘要：

  Macrophage scavenger receptors appear to play a major role in the clearance of oxidized phospholipid (OxPL) products. Discrete peptide-phospholipid conjugates with the phosphatidylcholine headgroup have been shown to exhibit binding affinity for these receptors. We report the preparation of a water-soluble, stable peptide-phospholipid conjugate (9) that possesses the necessary physical properties to enable more detailed study of the role(s) of OxPL in metabolic disease.

  DOI：

  10.1021/jm300685s

文献信息

• Design and Synthesis of a Stable Oxidized Phospholipid Mimic with Specific Binding Recognition for Macrophage Scavenger Receptors
  作者：William W. Turner、Karsten Hartvigsen、Agnes Boullier、Erica N. Montano、Joseph L. Witztum、Michael S. VanNieuwenhze

  DOI：10.1021/jm300685s

  日期：2012.9.27

  Macrophage scavenger receptors appear to play a major role in the clearance of oxidized phospholipid (OxPL) products. Discrete peptide-phospholipid conjugates with the phosphatidylcholine headgroup have been shown to exhibit binding affinity for these receptors. We report the preparation of a water-soluble, stable peptide-phospholipid conjugate (9) that possesses the necessary physical properties to enable more detailed study of the role(s) of OxPL in metabolic disease.