3',4'-bis(bis(2-tert-butoxy-2-oxoethyl)amino)biphenyl-4-carboxylic acid | 1610690-91-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3',4'-bis(bis(2-tert-butoxy-2-oxoethyl)amino)biphenyl-4-carboxylic acid
• CAS: 1610690-91-9
• 化学式: C₃₇H₅₂N₂O₁₀
• 分子量: 684.827
• InChiKey: RJCQRCQVTWPRRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  49.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  148.98
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3',4'-bis(bis(2-tert-butoxy-2-oxoethyl)amino)biphenyl-4-carboxylic acid 、 β-lactosylamine 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 24.08h， 以61%的产率得到tetra-tert-butyl 2,2',2'',2'''-((4'-((1-deoxy-D-lactopyranoside-1-yl)carbamoyl)[1,1'-biphenyl]-3,4-diyl)bis(azanetriyl))tetraacetate
  参考文献：
  名称：

  Lanthanide-Chelating Carbohydrate Conjugates Are Useful Tools To Characterize Carbohydrate Conformation in Solution and Sensitive Sensors to Detect Carbohydrate–Protein Interactions

  摘要：

  The increasing interest in the functional versatility of glycan epitopes in cellular glycoconjugates calls for developing sensitive methods to define carbohydrate conformation in solution and to characterize protein-carbohydrate interactions. Measurements of pseudocontact shifts in the presence of a paramagnetic cation can provide such information. In this work, the energetically privileged conformation of a disaccharide (lactose as test case) was experimentally inferred by using a synthetic carbohydrate conjugate bearing a lanthanide binding tag. In addition, the binding of lactose to a biomedically relevant receptor (the human adhesion/growth-regulatory lectin galectin-3) and its consequences in structural terms were defined, using Dy3+, Tb3+, and Tm3+. The described approach, complementing the previously tested protein tagging as a way to exploit paramagnetism, enables to detect binding, even weak interactions, and to characterize in detail topological aspects useful for physiological ligands and mimetics in drug design.

  DOI：

  10.1021/ja502406x
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 4-iodobenzoate 在 potassium phosphate 、 四丁基氟化铵 、 palladium diacetate 、 2-(二环己基膦基)联苯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 3',4'-bis(bis(2-tert-butoxy-2-oxoethyl)amino)biphenyl-4-carboxylic acid
  参考文献：
  名称：

  Lanthanide-Chelating Carbohydrate Conjugates Are Useful Tools To Characterize Carbohydrate Conformation in Solution and Sensitive Sensors to Detect Carbohydrate–Protein Interactions

  摘要：

  The increasing interest in the functional versatility of glycan epitopes in cellular glycoconjugates calls for developing sensitive methods to define carbohydrate conformation in solution and to characterize protein-carbohydrate interactions. Measurements of pseudocontact shifts in the presence of a paramagnetic cation can provide such information. In this work, the energetically privileged conformation of a disaccharide (lactose as test case) was experimentally inferred by using a synthetic carbohydrate conjugate bearing a lanthanide binding tag. In addition, the binding of lactose to a biomedically relevant receptor (the human adhesion/growth-regulatory lectin galectin-3) and its consequences in structural terms were defined, using Dy3+, Tb3+, and Tm3+. The described approach, complementing the previously tested protein tagging as a way to exploit paramagnetism, enables to detect binding, even weak interactions, and to characterize in detail topological aspects useful for physiological ligands and mimetics in drug design.

  DOI：

  10.1021/ja502406x