2-deoxy-6-O-{2-deoxy-4-O-phosphono-2-[(R)-3-tetradecanoyloxytetradecanamido]-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-β-D-glucopyranosyl}-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-tetradecanoyloxytetradecanamido]-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-6-O-{2-deoxy-4-O-phosphono-2-[(R)-3-tetradecanoyloxytetradecanamido]-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-β-D-glucopyranosyl}-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-tetradecanoyloxytetradecanamido]-D-glucopyranose
• 英文别名: [(3R,4R,5S,6R)-2,5-dihydroxy-6-[[(2R,3R,4R,5S,6R)-6-(hydroxymethyl)-5-phosphonooxy-3-[[(3R)-3-tetradecanoyloxytetradecanoyl]amino]-4-[(3R)-3-tetradecanoyloxytetradecanoyl]oxyoxan-2-yl]oxymethyl]-3-[[(3R)-3-tetradecanoyloxytetradecanoyl]amino]oxan-4-yl] (3R)-3-hydroxytetradecanoate
• 化学式: C₁₁₀H₂₀₇N₂O₂₃P
• 分子量: 1956.83
• InChiKey: GNRKGDKPHXPDOQ-SHNNZCGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  34.8
• 重原子数：
  136
• 可旋转键数：
  102
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  365
• 氢给体数：
  8
• 氢受体数：
  23

反应信息

• 作为产物：
  描述：

  C₁₅₂H₂₄₃N₂O₂₃P 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 24.0h， 以75%的产率得到2-deoxy-6-O-{2-deoxy-4-O-phosphono-2-[(R)-3-tetradecanoyloxytetradecanamido]-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-β-D-glucopyranosyl}-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-tetradecanoyloxytetradecanamido]-D-glucopyranose
  参考文献：
  名称：

  具有不同的3-O取代的单磷酰脂质A类似物：合成和有效的佐剂活性。

  摘要：

  结构确定的免疫刺激佐剂在新一代疫苗的开发中起重要作用。这里描述了在还原糖的3-O-位具有不同取代的三种单磷酰基脂质A类似物（1-3）的合成及其有效的免疫刺激佐剂活性。合成涉及糖基化受体苄基3，4-二-O-苄基-2-脱氧-2-[（R）-3-十四烷酰氧基四癸酰胺基]-β-D-葡萄糖吡喃糖苷（16）和苄基3-O-的制备。烯丙基-4-O-苄基-2-脱氧-2-[（R）-3-十四烷酰氧基四癸酰胺基]-β-D-glu复制糖苷（17）。供体4,6-二-O-亚苄基-2-脱氧-2-（2'，2'，2'-三氯乙氧基羰基氨基）-α-d-gl核糖基三氯乙酰亚氨酸酯（21）与受体16和17之间的糖基化反应提供所需的beta-（1-> 6）-连接的二糖22和23。4，6-二-O-亚苄基的选择性还原性开环，在4'-羟基上安装磷酸基团，以及最终的整体脱苄基作用产生了设计的单磷酰基脂质A类似物1-3。在全合成脂质体疫苗系统的离

  DOI：

  10.1016/j.carres.2007.01.012

文献信息

• SYNTHETIC LIPID-A ANALOGS AND USES THEREOF
  申请人：BIOMIRA, INC.

  公开号：EP1232168A2

  公开（公告）日：2002-08-21
• [EN] SYNTHETIC LIPID-A ANALOGS AND USES THEREOF<br/>[FR] ANALOGUES DE LIPIDE-A DE SYNTHESE ET LEUR UTILISATION
  申请人：BIOMIRA INC

  公开号：WO2001036433A2

  公开（公告）日：2001-05-25

  New synthetic Lipid-A analogs based on monosaccharide (1) and disaccharide (2) derivatives were designed and prepared in the present invention. Both structures (1) and (2) incorporate novel lipid structures (3) and (4) that are not found in nature. Also, novel disaccharide Lipid-A structures (2) that incorporate novel contingents of uniform lipids and where R1, R4 and R5 are the same substitution group of structure (III) were synthesized. Liposome formulations containing totally synthetic components such as synthetic Lipid-A and synthetic lipopeptide derived from tumor-associated MUC1 mucin are described along with their therapeutic utility. Comparative test results of immunostimulating properties and toxicity of Lipid-A analogs (1) and (2) are included.