| 847229-69-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 847229-69-0
• 化学式: C₇₆H₈₉NO₁₅Si
• 分子量: 1284.63
• InChiKey: UBVHAVYVQKNYSE-UESJNIEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.72
• 重原子数：
  93.0
• 可旋转键数：
  33.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  176.21
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  2,2,2-三氯代亚氨逐乙酸-4-甲氧基苄酯 、 在 三氟甲磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Biological Evaluation of Rationally Modified Analogs of the H-Type II Blood Group Trisaccharide. A Correlation between Solution Conformation and Binding Affinity

  摘要：

  The role of local steric influences on the solution conformation and the biological activity of the II-type II blood group determinant 1 has been evaluated using structurally modified trisaccharides 2-4 and their corresponding C1-substituted C-glycosides 5-8 as conformational models. The preference of the C-glycosidic bond to adopt the gauche ''exo-anomeric'' conformation and the removal of destabilizing 1,3-diaxial-like interactions on the C-aglyconic bond have been used to create predictable conformational characteristics in C-trisaccharides 5-8. Vicinal coupling constants from H-1 NMR spectroscopy and 2D NOESY spectroscopy demonstrate that structural modifications in the C-trisaccharides result in large changes in their conformational preferences. To test the impact of solution conformation on receptor-ligand recognition, the affinities of compounds 1-8 toward the lectin I of Ulex europaeus (UEA-I) have been investigated using a quantitative binding assay. The binding affinities of the II-type II trisaccharide 1 and the corresponding carbon analog 5 are virtually identical. The activities of the structurally modified C-trisaccharides 6-8 decrease sharply relative to the unmodified C-trisaccharide 5, correlating conformation to binding affinity. A parallel gradient in binding affinity is observed for the O-trisaccharides 1-4. The selectivity of UEA-I for epitopes 1-8 validates the assumption that its receptor site largely defines a bound conformation for the substrates, and establishes that the conformational behavior of O-glycosides such as 1-4 is similar to that of C-glycosides such as 5-8.

  DOI：

  10.1021/ja00142a008
• 作为产物：
  描述：

  Carbonic acid allyl ester (2R,3S,4R,5R,6R)-6-[9-(tert-butyl-diphenyl-silanyloxy)-nonyloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl ester 在 四(三苯基膦)钯 、 甲酸 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 正丁胺 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Biological Evaluation of Rationally Modified Analogs of the H-Type II Blood Group Trisaccharide. A Correlation between Solution Conformation and Binding Affinity

  摘要：

  The role of local steric influences on the solution conformation and the biological activity of the II-type II blood group determinant 1 has been evaluated using structurally modified trisaccharides 2-4 and their corresponding C1-substituted C-glycosides 5-8 as conformational models. The preference of the C-glycosidic bond to adopt the gauche ''exo-anomeric'' conformation and the removal of destabilizing 1,3-diaxial-like interactions on the C-aglyconic bond have been used to create predictable conformational characteristics in C-trisaccharides 5-8. Vicinal coupling constants from H-1 NMR spectroscopy and 2D NOESY spectroscopy demonstrate that structural modifications in the C-trisaccharides result in large changes in their conformational preferences. To test the impact of solution conformation on receptor-ligand recognition, the affinities of compounds 1-8 toward the lectin I of Ulex europaeus (UEA-I) have been investigated using a quantitative binding assay. The binding affinities of the II-type II trisaccharide 1 and the corresponding carbon analog 5 are virtually identical. The activities of the structurally modified C-trisaccharides 6-8 decrease sharply relative to the unmodified C-trisaccharide 5, correlating conformation to binding affinity. A parallel gradient in binding affinity is observed for the O-trisaccharides 1-4. The selectivity of UEA-I for epitopes 1-8 validates the assumption that its receptor site largely defines a bound conformation for the substrates, and establishes that the conformational behavior of O-glycosides such as 1-4 is similar to that of C-glycosides such as 5-8.

  DOI：

  10.1021/ja00142a008