O-bis(phenyloxy)phosphoryl Nα-[(R)-3-dodecanoyloxytetradecanoyl] DL-homoserine N-{(4R)-5-hydroxy-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide | 253587-01-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O-bis(phenyloxy)phosphoryl Nα-[(R)-3-dodecanoyloxytetradecanoyl] DL-homoserine N-{(4R)-5-hydroxy-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide
• 英文别名: [(3R)-1-[[4-diphenoxyphosphoryloxy-1-[[(4R)-5-hydroxy-4-[[(3R)-3-phenylmethoxytetradecanoyl]amino]pentyl]amino]-1-oxobutan-2-yl]amino]-1-oxotetradecan-3-yl] dodecanoate
• CAS: 253587-01-8
• 化学式: C₆₈H₁₁₀N₃O₁₁P
• 分子量: 1176.61
• InChiKey: QSRJNZILTMIBDR-GPBRYYBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.2
• 重原子数：
  83
• 可旋转键数：
  55
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  188
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  O-bis(phenyloxy)phosphoryl Nα-[(R)-3-dodecanoyloxytetradecanoyl] DL-homoserine N-{(4R)-5-hydroxy-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以74%的产率得到O-bis(phenyloxy)phosphoryl N-[(R)-3-dodecanoyloxytetradecanoyl] DL-homoserine N-{(4R)-5-hydroxy-4-[(R)-3-hydroxytetradecanoylamino]pentyl}amide
  参考文献：
  名称：

  Synthesis and Immunobiological Activity of an Original Series of Acyclic Lipid A Mimics Based on a Pseudodipeptide Backbone

  摘要：

  N-delta-L-Homoserinyl-D-ornithinol pseudodipeptides N-acylated with typical Escherichia coli lipid A fatty acid residues and mono-O- or bis-O-phosphorylated have been prepared and their properties investigated. The derivatives carrying two phosphate groups were found to be inducers of NO production. In addition, while they were unable to induce significantly the production of interleukin-6 (IL-6) by human PBMC cells, these compounds behaved also as potent antagonists of LPS-induced IL-6 production in the same human cells system. In conclusion, the molecules described here are the first members of an original class of immunobiologically active lipid A mimics based on an acyclic pseudodipeptide backbone carrying only the essential functionalities of the parent lipid A structure (OM-174). As the products exhibit very low endotoxicity and pyrogenicity, this class of lipid A mimics therefore opens a new generation of immunoadjuvants that possibly could reach clinical applications.

  DOI：

  10.1021/jm060482a
• 作为产物：
  描述：

  R-(3)-苄氧基肉豆蔻酸 在 palladium on activated charcoal N-甲基吗啉 、 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline 、 氢气 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 O-bis(phenyloxy)phosphoryl Nα-[(R)-3-dodecanoyloxytetradecanoyl] DL-homoserine N-{(4R)-5-hydroxy-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide
  参考文献：
  名称：

  Synthesis and Immunobiological Activity of an Original Series of Acyclic Lipid A Mimics Based on a Pseudodipeptide Backbone

  摘要：

  N-delta-L-Homoserinyl-D-ornithinol pseudodipeptides N-acylated with typical Escherichia coli lipid A fatty acid residues and mono-O- or bis-O-phosphorylated have been prepared and their properties investigated. The derivatives carrying two phosphate groups were found to be inducers of NO production. In addition, while they were unable to induce significantly the production of interleukin-6 (IL-6) by human PBMC cells, these compounds behaved also as potent antagonists of LPS-induced IL-6 production in the same human cells system. In conclusion, the molecules described here are the first members of an original class of immunobiologically active lipid A mimics based on an acyclic pseudodipeptide backbone carrying only the essential functionalities of the parent lipid A structure (OM-174). As the products exhibit very low endotoxicity and pyrogenicity, this class of lipid A mimics therefore opens a new generation of immunoadjuvants that possibly could reach clinical applications.

  DOI：

  10.1021/jm060482a