2,2',2'',2'''-((4'-((1-deoxy-D-lactopyranoside-1-yl)carbamoyl)[1,1'-biphenyl]-3,4-diyl)bis(azanetriyl))tetraacetic acid | 1610690-89-5

• 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: 2,2',2'',2'''-((4'-((1-deoxy-D-lactopyranoside-1-yl)carbamoyl)[1,1'-biphenyl]-3,4-diyl)bis(azanetriyl))tetraacetic acid
• 英文别名: 2-[2-[bis(carboxymethyl)amino]-N-(carboxymethyl)-4-[4-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]carbamoyl]phenyl]anilino]acetic acid
• CAS: 1610690-89-5
• 化学式: C₃₃H₄₁N₃O₁₉
• 分子量: 783.697
• InChiKey: STIYSMNPFUFJML-ZPQGUEMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  55
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  354
• 氢给体数：
  12
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  lactosyl azide 在 甲醇 、 三异丙基硅烷 、 palladium 10% on activated carbon 、 氢气 、 sodium methylate 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 46.58h， 生成 2,2',2'',2'''-((4'-((1-deoxy-D-lactopyranoside-1-yl)carbamoyl)[1,1'-biphenyl]-3,4-diyl)bis(azanetriyl))tetraacetic 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

文献信息

• Lanthanide-Chelating Carbohydrate Conjugates Are Useful Tools To Characterize Carbohydrate Conformation in Solution and Sensitive Sensors to Detect Carbohydrate–Protein Interactions
  作者：Ángeles Canales、Álvaro Mallagaray、M. Álvaro Berbís、Armando Navarro-Vázquez、Gema Domínguez、F. Javier Cañada、Sabine André、Hans-Joachim Gabius、Javier Pérez-Castells、Jesús Jiménez-Barbero

  DOI：10.1021/ja502406x

  日期：2014.6.4

  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.