甲基 2-(乙酰氨基)-2-脱氧-3-O-beta-D-吡喃半乳糖基-beta-D-吡喃半乳糖苷 | 88274-25-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 甲基 2-(乙酰氨基)-2-脱氧-3-O-beta-D-吡喃半乳糖基-beta-D-吡喃半乳糖苷
• 中文别名: N-乙酰基-3-O-β-D-吡喃半乳糖基-β-D-半乳糖胺甲基糖苷；甲基2-(乙酰氨基)-2-脱氧-3-O-beta-D-吡喃半乳糖基-beta-D-吡喃半乳糖苷
• 英文名称: methyl β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-β-D-galactopyranoside
• 英文别名: β-D-Galp-(1<*>3)-α-D-GalpNAcOMe；Galβ(1-3)GalNAcβOMe；N-Acetyl-3-O-B-D-galactopyranosyl-B-D-GA；N-[(2R,3R,4R,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-methoxy-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 88274-25-3
• 化学式: C₁₅H₂₇NO₁₁
• 分子量: 397.379
• InChiKey: JPIHIQIYWZWIPU-NNPCJPQPSA-N

物化性质

• 沸点：
  743.3±60.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  187
• 氢给体数：
  7
• 氢受体数：
  11

安全信息

• WGK Germany：
  3

反应信息

• 作为产物：
  描述：

  methyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-β-D-glucopyranoside 在 吡啶 、 三氟化硼乙醚 、 sodium methylate 、 trifluoromethanesulfonic acid anhydride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 甲基 2-(乙酰氨基)-2-脱氧-3-O-beta-D-吡喃半乳糖基-beta-D-吡喃半乳糖苷
  参考文献：
  名称：

  Dissecting the Cholera Toxin−Ganglioside GM1 Interaction by Isothermal Titration Calorimetry

  摘要：

  The complex of cholera toxin and ganglioside GM1 is one of the highest affinity protein-carbohydrate interactions known. Herein, the GM1 pentasaccharide is dissected into smaller fragments to determine the contribution of each of the key monosaccharicle residues to the overall binding affinity. Displacement isothermal titration calorimetry (ITC) has allowed the measurement of all of the key thermodynamic parameters for even the lowest affinity fragment ligands. Analysis of the standard free energy changes using Jencks' concept of intrinsic free energies reveals that the terminal galactose and sialic acid residues contribute 54% and 44% of the intrinsic binding energy, respectively, despite the latter ligand having little appreciable affinity for the toxin. This analysis also provides an estimate of 25.8 kJ mol(-1) for the loss of independent translational and rotational degrees of freedom on complexation and presents evidence for an alternative binding mode for ganglioside GM2. The high affinity and selectivity of the GM1-cholera toxin interaction originates principally from the conformational preorganization of the branched pentasaccharide rather than through the effect of cooperativity, which is also reinvestigated by ITC.

  DOI：

  10.1021/ja0378207