4-((3-(((2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)propyl)amino)-4-oxobutanoic acid | 1202384-53-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-((3-(((2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)propyl)amino)-4-oxobutanoic acid
• CAS: 1202384-53-9
• 化学式: C₂₁H₃₂N₂O₁₂
• 分子量: 504.491
• InChiKey: URSVRNWJCWTYFH-RMLALMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.97
• 重原子数：
  35.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  192.86
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-{2-[2-(2-Aminoethoxy)ethoxy]ethyl}-5-(1,2-dithiolan-3-YL)pentanamide 、 4-((3-(((2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)propyl)amino)-4-oxobutanoic acid 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Lipoic Acid Glyco-Conjugates, a New Class of Agents for Controlling Nonspecific Adsorption of Blood Serum at Biointerfaces for Biosensor and Biomedical Applications

  摘要：

  The carbohydrate-derived lipoic acid derivatives were Studied as protein and cell resistant biomaterials. Six types of carbohydrates were examined for their abilities to reduce nonspecific adsorption of human serum and Hela cell using quartz crystal microbalance. Our data Suggested that the Structures of carbohydrates play an important role in resisting nonspecific binding. Specifically, the resistance was found to increase in the order lipoic fucose < lipoic mannose < lipoic N-acetyl glucosamine < lipoic glucose < lipoic sialic acid < lipoic galactose, where lipoic galactose derivative resisted most nonspecific adsorption. Furthermore, the combination of lipoic galactose and BSA was the most effective in reducing the adsorption of even undiluted human serum and the attachment of Hela cells while allowing specific binding. Several control experiments have demonstrated that the resistant-ability of mixed lipoic galactose and BSA was comparable to the best known system for decreasing nonspecific adsorption.

  DOI：

  10.1021/la903261j
• 作为产物：
  描述：

  丁二酸酐 、 3-azidopropyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 4-((3-(((2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)propyl)amino)-4-oxobutanoic acid
  参考文献：
  名称：

  Lipoic Acid Glyco-Conjugates, a New Class of Agents for Controlling Nonspecific Adsorption of Blood Serum at Biointerfaces for Biosensor and Biomedical Applications

  摘要：

  The carbohydrate-derived lipoic acid derivatives were Studied as protein and cell resistant biomaterials. Six types of carbohydrates were examined for their abilities to reduce nonspecific adsorption of human serum and Hela cell using quartz crystal microbalance. Our data Suggested that the Structures of carbohydrates play an important role in resisting nonspecific binding. Specifically, the resistance was found to increase in the order lipoic fucose < lipoic mannose < lipoic N-acetyl glucosamine < lipoic glucose < lipoic sialic acid < lipoic galactose, where lipoic galactose derivative resisted most nonspecific adsorption. Furthermore, the combination of lipoic galactose and BSA was the most effective in reducing the adsorption of even undiluted human serum and the attachment of Hela cells while allowing specific binding. Several control experiments have demonstrated that the resistant-ability of mixed lipoic galactose and BSA was comparable to the best known system for decreasing nonspecific adsorption.

  DOI：

  10.1021/la903261j