1-deoxy-1-[2-(1,2-ditetradecanoyl-sn-glycero-3-phosphooxy)ethylamino]-D-fructose | 193066-98-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-deoxy-1-[2-(1,2-ditetradecanoyl-sn-glycero-3-phosphooxy)ethylamino]-D-fructose
• CAS: 193066-98-7
• 化学式: C₃₉H₇₆NO₁₃P
• 分子量: 798.005
• InChiKey: RYNMQJGCUSLYNY-IACRFGEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.37
• 重原子数：
  54.0
• 可旋转键数：
  36.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  210.54
• 氢给体数：
  6.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  1-deoxy-1-[2-(1,2-ditetradecanoyl-sn-glycero-3-phosphooxy)ethylamino]-D-fructose 在 Tris buffer 、 sodium dodecyl-sulfate 、 phospholipase D 作用下， 以 甲醇 、 水 为溶剂， 反应 17.5h， 生成 E-1-deoxy-1-(2-hydroxyethylamino)-D-fructose (3-methylbenzothiazolin-2-ylidene)hydrazone acetic acid salt
  参考文献：
  名称：

  Amadori products from model reactions of d-glucose with phosphatidyl ethanolamine—Independent synthesis and identification of 1-deoxy-1-(2-hydroxyethylamino)-d-fructose derivatives

  摘要：

  Nonenzymatic glycosylation of aminophospholipids is supposed to play an important role for lipid oxidation in vivo. Investigations are reported on how the Amadori products 1-deoxy-1-[2-(1,2-ditetradecanoyl-sn-glycero-3-phosphooxy)ethylamino]-D-fructose (4) and 1-deoxy-1-[2-(1,2-dihexadecanoyl-sn-glycero-3-phosphooxy)ethylamino]-D-fructose (5) can be identified from model reactions of D-glucose and phosphatidyl ethanolamine. Independent syntheses and unequivocal structural characterization are given for the E/Z-1-deoxy-1-(2-hydroxyethylamino)-D-fructose (3-methylbenzothiazolin-2-ylidene)hydrazone (12a,b) and the peracetylated E/Z-1-deoxy-1-(2-hydroxyethylamino)-D-fructose O-methyloxime (13a,b). Chromatographic and spectroscopic data for these 1-deoxy-1-(2-hydroxyethylamino)-D-fructose derivatives were established by either GLC-MS or HPLC with diode array detection (DAD). Phosphatidyl ethanolamine and D-glucose were incubated at 37 degrees C, pH 7.4, in neat buffer or ethanol-buffer mixtures for four weeks, and the phospholipid fraction was purified on a C18 solid-phase extraction column. The phosphatidic acid was cleaved with phospholipase D and the free 1-deoxy-1-(2-hydroxyethylamino)-D-fructose derivatized to give 12a,b or 13a,b, respectively. Both these derivatives could be identified from all incubations by GLC-MS and HPLC-DAD analyses, respectively. Formation of 4 and 5 is favored in ethanol-buffer reaction mixtures relative to those in buffer solution only. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00090-6
• 作为产物：
  描述：

  D-葡萄糖 、 1,2-十四酰基磷脂酰乙醇胺 在 phosphate buffer 作用下， 以 乙醇 、 水 为溶剂， 生成 1-deoxy-1-[2-(1,2-ditetradecanoyl-sn-glycero-3-phosphooxy)ethylamino]-D-fructose
  参考文献：
  名称：

  Amadori products from model reactions of d-glucose with phosphatidyl ethanolamine—Independent synthesis and identification of 1-deoxy-1-(2-hydroxyethylamino)-d-fructose derivatives

  摘要：

  Nonenzymatic glycosylation of aminophospholipids is supposed to play an important role for lipid oxidation in vivo. Investigations are reported on how the Amadori products 1-deoxy-1-[2-(1,2-ditetradecanoyl-sn-glycero-3-phosphooxy)ethylamino]-D-fructose (4) and 1-deoxy-1-[2-(1,2-dihexadecanoyl-sn-glycero-3-phosphooxy)ethylamino]-D-fructose (5) can be identified from model reactions of D-glucose and phosphatidyl ethanolamine. Independent syntheses and unequivocal structural characterization are given for the E/Z-1-deoxy-1-(2-hydroxyethylamino)-D-fructose (3-methylbenzothiazolin-2-ylidene)hydrazone (12a,b) and the peracetylated E/Z-1-deoxy-1-(2-hydroxyethylamino)-D-fructose O-methyloxime (13a,b). Chromatographic and spectroscopic data for these 1-deoxy-1-(2-hydroxyethylamino)-D-fructose derivatives were established by either GLC-MS or HPLC with diode array detection (DAD). Phosphatidyl ethanolamine and D-glucose were incubated at 37 degrees C, pH 7.4, in neat buffer or ethanol-buffer mixtures for four weeks, and the phospholipid fraction was purified on a C18 solid-phase extraction column. The phosphatidic acid was cleaved with phospholipase D and the free 1-deoxy-1-(2-hydroxyethylamino)-D-fructose derivatized to give 12a,b or 13a,b, respectively. Both these derivatives could be identified from all incubations by GLC-MS and HPLC-DAD analyses, respectively. Formation of 4 and 5 is favored in ethanol-buffer reaction mixtures relative to those in buffer solution only. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00090-6