1-deoxy-1-[2-(1,2-dihexadecanoyl-sn-glycero-3-phosphooxy)ethylamino]-D-fructose | 193066-99-8

• 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-dihexadecanoyl-sn-glycero-3-phosphooxy)ethylamino]-D-fructose
• 英文别名: [(2R)-2-hexadecanoyloxy-3-[hydroxy-[2-[[(2R,3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methylamino]ethoxy]phosphoryl]oxypropyl] hexadecanoate
• CAS: 193066-99-8
• 化学式: C₄₃H₈₄NO₁₃P
• 分子量: 854.113
• InChiKey: MILIBGPOWWEDIF-IEAGFSAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  58
• 可旋转键数：
  42
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  211
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1-deoxy-1-[2-(1,2-dihexadecanoyl-sn-glycero-3-phosphooxy)ethylamino]-D-fructose 在 Tris buffer 、 sodium dodecyl-sulfate 、 phospholipase D 作用下， 以 水 为溶剂， 反应 1.5h， 生成 1-deoxy-1-(2-hydroxyethylamino)-D-fructose hydrochloride
  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：

  以 甲醇 、 aq. phosphate buffer 、 水 为溶剂， 反应 8.0h， 生成 1-deoxy-1-[2-(1,2-dihexadecanoyl-sn-glycero-3-phosphooxy)ethylamino]-D-fructose
  参考文献：
  名称：

  高磷脂食品在热处理过程中糖化磷脂酰乙醇胺形成途径的初步研究

  摘要：

  通过设计 1,2-二棕榈酰-sn-甘油-3-磷酸乙醇胺 (DPPE)-葡萄糖模型系统，在 40 至 100 °C 下加热 8 小时，研究了食品衍生的糖化磷脂酰乙醇胺 (PE) 在热过程中的形成。糖化PE的主要产物采用高效液相色谱-串联质谱(HPLC-MS/MS)测定。结果表明，DPPE的糖化形成了三种主要的糖化化合物：阿马多里-糖化-1,2-二棕榈酰-sn-甘油-3-磷酸乙醇胺（Amadori-DPPE）、羧甲基-1,2-二棕榈酰-sn-甘油-3-磷酸乙醇胺 (CM-DPPE) 和 carboxyethyl-1,2-dipalmitoyl- sn-glycero-3-磷酸乙醇胺 (CE-DPPE)。Amadori-DPPE 被鉴定为通过在高温和延长孵育时间下氧化裂解糖化极性头部基团来生成 CM-DPPE。此外，在热处理过程中，葡萄糖的反醛醇反应导致形成两种反应性二羰基中间体：乙二醛 (GO)

  DOI：

  10.1039/c8ra01072b

文献信息

• A preliminary study on the formation pathways of glycated phosphatidylethanolamine of food rich in phospholipid during the heat-processing
  作者：Qingna Lin、Lipeng Han、Guoqin Liu、Weiwei Cheng、Liqing Wang

  DOI：10.1039/c8ra01072b

  日期：——

  through oxidative cleavage of glycated polar head group under high temperature and extended incubation time. Additionally, during thermal processing, retro-aldol reactions of glucose led to the formation of two reactive dicarbonyl intermediates: glyoxal (GO) and methylglyoxal (MGO), both of them reacted with amino group of DPPE to form CM-DPPE and CE-DPPE, respectively. Thus, the formation pathways

  通过设计 1,2-二棕榈酰-sn-甘油-3-磷酸乙醇胺 (DPPE)-葡萄糖模型系统，在 40 至 100 °C 下加热 8 小时，研究了食品衍生的糖化磷脂酰乙醇胺 (PE) 在热过程中的形成。糖化PE的主要产物采用高效液相色谱-串联质谱(HPLC-MS/MS)测定。结果表明，DPPE的糖化形成了三种主要的糖化化合物：阿马多里-糖化-1,2-二棕榈酰-sn-甘油-3-磷酸乙醇胺（Amadori-DPPE）、羧甲基-1,2-二棕榈酰-sn-甘油-3-磷酸乙醇胺 (CM-DPPE) 和 carboxyethyl-1,2-dipalmitoyl- sn-glycero-3-磷酸乙醇胺 (CE-DPPE)。Amadori-DPPE 被鉴定为通过在高温和延长孵育时间下氧化裂解糖化极性头部基团来生成 CM-DPPE。此外，在热处理过程中，葡萄糖的反醛醇反应导致形成两种反应性二羰基中间体：乙二醛 (GO)
• Amadori products from model reactions of d-glucose with phosphatidyl ethanolamine—Independent synthesis and identification of 1-deoxy-1-(2-hydroxyethylamino)-d-fructose derivatives
  作者：Markus O. Lederer、Claudia M. Dreisbusch、Rainer M. Bundschuh

  DOI：10.1016/s0008-6215(97)00090-6

  日期：1997.6

  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.