2,3-diamino-1-O-<(R)-4-carboxy-4-<(R)-3-hydroxytetradecanamido>butanoyl>-2,3-bis-N-<(R)-3-hydroxytetradecanoyl>-2,3-dideoxy-α-D-glucopyranose | 143060-85-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-diamino-1-O-<(R)-4-carboxy-4-<(R)-3-hydroxytetradecanamido>butanoyl>-2,3-bis-N-<(R)-3-hydroxytetradecanoyl>-2,3-dideoxy-α-D-glucopyranose
• 英文别名: (2R)-5-[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis[[(3R)-3-hydroxytetradecanoyl]amino]oxan-2-yl]oxy-2-[[(3R)-3-hydroxytetradecanoyl]amino]-5-oxopentanoic acid
• CAS: 143060-85-9
• 化学式: C₅₃H₉₉N₃O₁₃
• 分子量: 986.381
• InChiKey: ZCJNQZQQACSOND-KHKXJKFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  69
• 可旋转键数：
  46
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  261
• 氢给体数：
  9
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  2,3-diamino-4,6-O-benzylidene-1-O-<(R)-4-<(benzyloxy)carbonyl>-4-<(R)-3-(benzyloxy)tetradecanamido>butanoyl>-2,3-bis<(R)-3-(benzyloxy)tetradecanoyl>-2,3-dideoxy-α-D-glucopyranose 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 2,3-diamino-1-O-<(R)-4-carboxy-4-<(R)-3-hydroxytetradecanamido>butanoyl>-2,3-bis-N-<(R)-3-hydroxytetradecanoyl>-2,3-dideoxy-α-D-glucopyranose
  参考文献：
  名称：

  Acyclic analogs of lipid A: synthesis and biological activities.

  摘要：

  The synthesis of a series of novel acyclic analogues of lipid A, the lipophilic terminal of lipopolysaccharide (LPS), is reported. In these compounds, the reducing glucose unit of lipid A has been replaced by an acyclic analogue unit (abbreviated as AAU) consisting of a spacer (of varying length), an (R)-3-hydroxytetradecanamido moiety (of varying configuration at the carbon of attachment), and a CO2H group. The AAU has been attached to the anomeric carbon of the nonreducing glucose unit of lipid A, either through glycosidic linkage or through an acyl linkage. Further, amide isosteres of these acyclic analogues have been prepared using suitably protected 2,3-diamino-2,3-dideoxyglucose instead of 2-amino-2-deoxyglucose. All the compounds were well characterized and were tested for their ability to induce TNF-alpha in mouse bone marrow-derived macrophages, to enhance nonspecific resistance to infection in mice and to induce endotoxic shock in mice. The results showed a dramatic dependence, for the first time, on the length of the spacer and on the configuration of the carbon bearing the amido group in the AAU part of the analogues.

  DOI：

  10.1021/jm00097a003

文献信息

• Acyclic analogs of lipid A: synthesis and biological activities.
  作者：Murty A. R. C. Bulusu、Peter Waldstaetten、Johannes Hildebrandt、Eberhard Schuetze、Gerhard Schulz

  DOI：10.1021/jm00097a003

  日期：1992.9

  The synthesis of a series of novel acyclic analogues of lipid A, the lipophilic terminal of lipopolysaccharide (LPS), is reported. In these compounds, the reducing glucose unit of lipid A has been replaced by an acyclic analogue unit (abbreviated as AAU) consisting of a spacer (of varying length), an (R)-3-hydroxytetradecanamido moiety (of varying configuration at the carbon of attachment), and a CO2H group. The AAU has been attached to the anomeric carbon of the nonreducing glucose unit of lipid A, either through glycosidic linkage or through an acyl linkage. Further, amide isosteres of these acyclic analogues have been prepared using suitably protected 2,3-diamino-2,3-dideoxyglucose instead of 2-amino-2-deoxyglucose. All the compounds were well characterized and were tested for their ability to induce TNF-alpha in mouse bone marrow-derived macrophages, to enhance nonspecific resistance to infection in mice and to induce endotoxic shock in mice. The results showed a dramatic dependence, for the first time, on the length of the spacer and on the configuration of the carbon bearing the amido group in the AAU part of the analogues.