(2R)-2-{(2S,3R,4S,5S,6R)-2-[(2R,3R)-1,4-dimethoxy-1,4-dioxo-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)butan-2-yloxy]-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy}-3-phenylpropanoic acid | 1403603-68-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R)-2-{(2S,3R,4S,5S,6R)-2-[(2R,3R)-1,4-dimethoxy-1,4-dioxo-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)butan-2-yloxy]-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy}-3-phenylpropanoic acid
• 英文别名: (R)-2-((2S,3R,4S,5S,6R)-2-((2R,3R)-1,4-dimethoxy-1,4-dioxo-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)butan-2-yloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy)-3-phenylpropanoic acid；(2R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R)-1,4-dimethoxy-1,4-dioxo-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxybutan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3-phenylpropanoic acid
• CAS: 1403603-68-8
• 化学式: C₂₇H₃₈O₁₇
• 分子量: 634.589
• InChiKey: OBGSYIUACCHCHT-RVTKUGSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  257
• 氢给体数：
  7
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  1-硫-乙基-2,3,4-三-氧-苄基-b-L-硫代呋喃岩藻糖苷 在 palladium 10% on activated carbon 、 camphor-10-sulfonic acid 、 氢气 、 sodium methylate 、 二正丁基氧化锡 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 、 1,4-二甲基环己烷 为溶剂， 反应 15.25h， 生成 (2R)-2-{(2S,3R,4S,5S,6R)-2-[(2R,3R)-1,4-dimethoxy-1,4-dioxo-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)butan-2-yloxy]-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy}-3-phenylpropanoic acid
  参考文献：
  名称：

  A New Approach to Explore the Binding Space of Polysaccharide-Based Ligands: Selectin Antagonists

  摘要：

  The discovery of molecules that interfere with the binding of a ligand to a receptor remains a topic of great interest in medicinal chemistry. Herein, we report that a monosaccharide unit of a polysaccharide ligand can be replaced advantageously by a conformationally locked acyclic molecular entity. A cyclic component of the selectin ligand Sialyl Lewis(x), GlcNAc, is replaced by an acyclic tether, tartaric esters, which link two saccharide units. The conformational bias of this acyclic tether originates from the minimization of intramolecular dipole-dipole interaction and the gauche effect. The evaluation of the binding of these derivatives to P-selectin was measured by surface plasmon resonance spectroscopy. The results obtained in our pilot study suggest that the discovery of tunable tethers could facilitate the exploration of the carbohydrate recognition domain of various receptors.

  DOI：

  10.1021/ml300263x

文献信息

• A New Approach to Explore the Binding Space of Polysaccharide-Based Ligands: Selectin Antagonists
  作者：Mickael Calosso、Daniel Charpentier、Marc Vaillancourt、Mohammed Bencheqroun、Gabrielle St-Pierre、Brian C. Wilkes、Yvan Guindon

  DOI：10.1021/ml300263x

  日期：2012.12.13

  The discovery of molecules that interfere with the binding of a ligand to a receptor remains a topic of great interest in medicinal chemistry. Herein, we report that a monosaccharide unit of a polysaccharide ligand can be replaced advantageously by a conformationally locked acyclic molecular entity. A cyclic component of the selectin ligand Sialyl Lewis(x), GlcNAc, is replaced by an acyclic tether, tartaric esters, which link two saccharide units. The conformational bias of this acyclic tether originates from the minimization of intramolecular dipole-dipole interaction and the gauche effect. The evaluation of the binding of these derivatives to P-selectin was measured by surface plasmon resonance spectroscopy. The results obtained in our pilot study suggest that the discovery of tunable tethers could facilitate the exploration of the carbohydrate recognition domain of various receptors.