9-[(2R,3R,4R,5R)-3-Acetylamino-5-[(2S,3R,5R,6R)-5-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid | 168844-74-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-[(2R,3R,4R,5R)-3-Acetylamino-5-[(2S,3R,5R,6R)-5-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid
• CAS: 168844-74-4
• 化学式: C₇₁H₈₇NO₁₆
• 分子量: 1210.47
• InChiKey: DGODDPDVIFIQIM-AZRLBIGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.46
• 重原子数：
  88.0
• 可旋转键数：
  35.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  186.39
• 氢给体数：
  2.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  9-[(2R,3R,4R,5R)-3-Acetylamino-5-[(2S,3R,5R,6R)-5-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid 在 palladium hydroxide - carbon 氢气 作用下， 以 甲醇 为溶剂， 生成 9-{(2R,3R,4R,5R)-3-Acetylamino-4-hydroxy-5-[(2S,3R,5R,6R)-5-hydroxy-6-hydroxymethyl-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yloxy}-nonanoic acid
  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：

  N-[(2R,3R,4R,5R)-5-[(2S,3R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4-(4-methoxy-benzyloxy)-2-(9-oxo-nonyloxy)-tetrahydro-pyran-3-yl]-acetamide 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 生成 9-[(2R,3R,4R,5R)-3-Acetylamino-5-[(2S,3R,5R,6R)-5-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid
  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