4-乙酰氨基苯基-三乙酰基-beta-D-葡萄糖苷酸甲酯 | 30824-21-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-乙酰氨基苯基-三乙酰基-beta-D-葡萄糖苷酸甲酯
• 中文别名: 4-乙酰氨基苯基-2,3,4-三-O-乙酰基-Β-D-葡糖苷酸甲酯
• 英文名称: methyl <4-(acetamido)phenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid>uronate
• 英文别名: methyl (p-acetamidophenyl 2,3,4-tri-O-acetyl-1-O-β-D-glucopyranosid)uronate；methyl 1-O-(4-acetamidophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate；O²,O³,O⁴-triacetyl-O¹-(4-acetylamino-phenyl)-β-D-glucopyranuronic acid methyl ester；O²,O³,O⁴-Triacetyl-O¹-(4-acetylamino-phenyl)-β-D-glucopyranuronsaeure-methylester；methyl (2S,3S,4S,5R,6S)-6-(4-acetamidophenoxy)-3,4,5-triacetyloxyoxane-2-carboxylate
• CAS: 30824-21-6
• 化学式: C₂₁H₂₅NO₁₁
• 分子量: 467.43
• InChiKey: CGFRFKWGBUUPFU-VDRZXAFZSA-N

物化性质

• 熔点：
  212-213°C dec.
• 沸点：
  590.5±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、乙醚、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-乙酰氨基苯基-三乙酰基-beta-D-葡萄糖苷酸甲酯 在 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 以85%的产率得到P-乙酰氨基苯-B-D-葡萄糖酸钠盐
  参考文献：
  名称：

  Preparation and characterisation of solid state forms of paracetamol-O-glucuronide

  摘要：

  The synthesis and crystallisation of the pharmaceutically important metabolite, paracetamol-O-glucuronide, is described. Hydrated and anhydrous forms of the target molecule have been characterised by PXRD, DSC and TGA. In addition, a methanol solvate has been analysed, including single crystal analysis, which represents the first structure solution for this system. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.12.018
• 作为产物：
  描述：

  4-氨基苯基吡喃己醛糖苷酸 在 吡啶 、 丙酮 、 silver(l) oxide 作用下， 生成 4-乙酰氨基苯基-三乙酰基-beta-D-葡萄糖苷酸甲酯
  参考文献：
  名称：

  Smith; Williams, Biochemical Journal, 1948, vol. 42, p. 538,541

  摘要：

  DOI：

文献信息

• N-Hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen
  作者：Ian C. Calder、Sandra J. Hart、Kevin Healey、Kathryn N. Ham

  DOI：10.1021/jm00140a014

  日期：1981.8

  The decomposition of N-hydroxyacetaminophen has been shown to occur via an initial first-order dehydration step to N-acetyl-p-benzoquinone imine with a rate constant at pH 7.6 of 8.66 x 10(-3) min-1 and a half-life of 80 min. This is followed by a complex reaction between the quinone imine and the N-hydroxy compound to ultimately yield p-nitrosophenol and acetaminophen. The glucuronide and sulfate conjugates

  已显示N-羟基对乙酰氨基酚的分解是通过最初的一阶脱水步骤而发生的，分解为N-乙酰基-对-苯醌亚胺，在pH 7.6时的速率常数为8.66 x 10（-3）min-1，半寿命80分钟。这之后是醌亚胺和N-羟基化合物之间的复杂反应，最终产生对亚硝基苯酚和对乙酰氨基酚。已经观察到N-羟基对乙酰氨基酚的葡糖醛酸苷和硫酸盐结合物是N-羟基对乙酰氨基酚的尿代谢产物。在对乙酰氨基酚的代谢产物中未发现N-羟基化代谢产物。这些结果已被解释为显示N-羟基对乙酰氨基酚不是对乙酰氨基酚的代谢产物。
• Chromatography of .BETA.-Glucuronidase from Bovine Liver. A Study of the Enzyme Binding Sites of Prepared Adsorbents.
  作者：Nobuko IINO、Kazuo YOSHIDA

  DOI：10.1248/cpb.40.1852

  日期：——

  β-Glucuronidase from bovine liver was adsorbed to the adsorbents prepared with CH-Sepharose 4B and either the competitive inhibitor or its analogs such as p-aminophenyl 1-thio-β-D-glucuronic acid, -glucoside, -galactoside, and N-acetyl glucosaminide. The adsorbed enzyme was eluted at 0.1 or 0.5 M NaCl by a stepwise gradient. Chromatography of the enzyme was also performed by using the adsorbents prepared with Epoxy-activated Sepharose 6B and amine compounds or other compounds.In order to see whether the hydroxyl groups of the sugar parts in the ligand are necessary for the adsorption of the enzyme, chromatography was performed by using the adsorbents prepared with sugar derivatives as the ligand. As a result, it was found that β-glucuronidase had an affinity for adsorbents prepared with either acetyl derivatives or methoxy derivatives of glycosides and CH-Sepharose 4B.From the results of elution of the enzyme with NaCl from adsorbents having amide bonding, it was clarified that the affinity of the enzyme for adsorbents without glycosides in the ligands correlated with acidity of the amide in the adsorbents.Hydrogen bond chromatography was performed with the prepared adsorbents. The enzyme was adsorbed under a high concentration of ammonium sulfate, and the elution of the adsorbed enzyme from adsorbents was examined by the degradation of salt. The enzyme was most easily eluted from aminoethyl 1-thio-β-D-glucuronic acid-CH Sepharose 4B at 0.9 M ammonium sulfate and at 0.5 M concentration of the salt with p-aminophenyl 1-thio-β-D-glucuronic acid-CH Sepharose 4B. Furthermore, the adsorbed enzyme was eluted by the addition of urea as well as ethylene glycol which are known as reagents which weaken hydrogen bonding. The results suggested that the interaction between the enzyme and the adsorbents with an amide bonding may be affected by the electrostatic force in the adsorbents under a high concentration of salt, although the electrostatic force decreases under the high concentration of salt.We also investigated whether or not the adsorbed enzyme was eluted by sodium cholate, cholic acid and triton X-100 known as hydrophobic reagents.it was assumed from the results of these chromatographiers that the presence of amide bonding in adsorbents with glycosides as the ligand may be essential for the adsorption of the enzyme and that the glycosidic parts of the ligands have an effect on adsorption, however, it may not be essential for adsorption.

  用 CH-Sepharose 4B 和竞争性抑制剂或其类似物（如对氨基苯基 1-硫代-β-D-葡萄糖醛酸、-葡萄糖苷、-半乳糖苷和 N-乙酰氨基葡萄糖苷）制备的吸附剂吸附牛肝脏中的β-葡萄糖醛酸酶。吸附的酶在 0.1 或 0.5 M NaCl 溶液中逐步梯度洗脱。为了了解配体中糖部分的羟基是否是吸附酶的必要条件，还使用了以糖衍生物为配体制备的吸附剂进行色谱分析。结果发现，β-葡糖醛酸酶对以糖苷的乙酰衍生物或甲氧基衍生物以及 CH-Sepharose 4B 制备的吸附剂具有亲和力。从具有酰胺键的吸附剂用 NaCl 洗脱酶的结果来看，酶对配体中不含有糖苷的吸附剂的亲和力与吸附剂中酰胺的酸性有关。在高浓度硫酸铵条件下吸附酶，并通过盐的降解检测吸附酶从吸附剂中的洗脱情况。在 0.9 M 硫酸铵和 0.5 M 浓度的对氨基苯基 1-thio-β-D-Glucuronic acid-CH Sepharose 4B 中，酶最容易从氨基乙基 1-thio-β-D-Glucuronic acid-CH Sepharose 4B 中洗脱出来。此外，加入尿素和乙二醇（众所周知，它们是削弱氢键的试剂）可洗脱吸附的酶。结果表明，在高浓度盐的条件下，酶与具有酰胺键的吸附剂之间的相互作用可能会受到吸附剂中静电力的影响，尽管在高浓度盐的条件下静电力会降低。根据这些色谱分析结果推测，以苷类化合物为配体的吸附剂中存在的酰胺键可能是吸附酶的必要条件，配体的苷类部分对吸附有影响，但也可能不是吸附的必要条件。
• JOHNSTON, DAVID;ANDREWS, RODERICK S.;ORMISTON, RAYMOND A., J. CHEM. RES. (S),(1988) N2, C. 406-407
  作者：JOHNSTON, DAVID、ANDREWS, RODERICK S.、ORMISTON, RAYMOND A.

  DOI：——

  日期：——