ammonium salt of adenosine 5'-phosphate P-(1-hexadecyl) ester | 74405-75-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: ammonium salt of adenosine 5'-phosphate P-(1-hexadecyl) ester
• 英文别名: ((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl hexadecyl hydrogen phosphate, ammonia salt；[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl hexadecyl hydrogen phosphate;azane
• CAS: 74405-75-7
• 化学式: C₂₆H₄₆N₅O₇P*H₃N
• 分子量: 588.685
• InChiKey: WULNWHFZQIXEQU-DGUBOJIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  40.0
• 可旋转键数：
  20.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  210.07
• 氢给体数：
  5.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  n-Hexadecylphosphorylcholine 、 腺苷 在 sodium acetate buffer 、 calcium chloride 、 phospholipase D 作用下， 以 氯仿 为溶剂， 反应 5.0h， 以43%的产率得到ammonium salt of adenosine 5'-phosphate P-(1-hexadecyl) ester
  参考文献：
  名称：

  Preparation and Characterization of Vesicles from Mono-n-alkyl Phosphates and Phosphonates

  摘要：

  The aggregation properties of different linear, single-chain alkyl phosphates and phosphonates in water were investigated at concentrations of up to 50 mM as a function of pH, focusing in particular on spontaneous vesicle formation. Under conditions where about half the molecules are monoionic and half the molecules are completely protonated (pH approximate to 2), n-dodecylphosphoric acid, n-decylphosphonic acid, and n-dodecylphosphonic acid spontaneously form vesicles at room temperature. For n-hexadecylphosphoric acid, stable vesicles only form above similar to 40 degrees C. The presence of vesicles was evidenced by light and electron microscopy and in the case of n-dodecylphosphoric acid by entrapment experiments using as water soluble probes glucose, dextran, and pepsin. The phase-transition temperature of vesicles of n-dodecylphosphoric acid was 2.3 degrees C, as determined by differential scanning calorimetry. For n-hexadecylphosphoryladenosine evidence for micelle formation has been obtained with a cmc of 20-50 mu M at 25 degrees C. In an experimental extension of the vesicle self-reproduction principles to phosphoamphiphiles, results are also presented on the alkaline hydrolysis of the water-insoluble di-n-decyl-4-nitrophenyl phosphate, which led to the formation of 4-nitrophenol and di-n-decyl phosphate, the latter being a known vesicle-forming amphiphile.

  DOI：

  10.1021/jp970898n

文献信息

• Smrt, Jiri; Hynie, Sixtus, Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 3, p. 927 - 932
  作者：Smrt, Jiri、Hynie, Sixtus

  DOI：——

  日期：——