2,6-anhydro-3-deoxy-7-O-[2-deoxy-2-[(R)-3-dodecanoyloxytetradecanamido]-6-O-methyl-4-O-phosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-β-D-glucopyranosyl]-3-[(R)-3-hydroxytetradecanamido]-D-glycero-D-ido-heptonic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-anhydro-3-deoxy-7-O-[2-deoxy-2-[(R)-3-dodecanoyloxytetradecanamido]-6-O-methyl-4-O-phosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-β-D-glucopyranosyl]-3-[(R)-3-hydroxytetradecanamido]-D-glycero-D-ido-heptonic acid
• 英文别名: (2S,3R,4R,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3-[[(3R)-3-dodecanoyloxytetradecanoyl]amino]-6-(methoxymethyl)-5-phosphonooxy-4-[(3R)-3-tetradecanoyloxytetradecanoyl]oxyoxan-2-yl]oxymethyl]-5-hydroxy-3-[[(3R)-3-hydroxytetradecanoyl]amino]-4-[(3R)-3-hydroxytetradecanoyl]oxyoxane-2-carboxylic acid
• 化学式: C₉₆H₁₇₉N₂O₂₃P
• 分子量: 1760.45
• InChiKey: XJDHBRVXWLPFFA-HSGZVRINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  28.2
• 重原子数：
  122
• 可旋转键数：
  88
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  在 platinum(IV) oxide 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以49%的产率得到2,6-anhydro-3-deoxy-7-O-[2-deoxy-2-[(R)-3-dodecanoyloxytetradecanamido]-6-O-methyl-4-O-phosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-β-D-glucopyranosyl]-3-[(R)-3-hydroxytetradecanamido]-D-glycero-D-ido-heptonic acid
  参考文献：
  名称：

  Lipid A-Type Pyrancarboxylic Acid Derivatives, their Synthesis and their Biological Activities

  摘要：

  Synthesis of lipid A-type pyrancarboxylic acid derivatives, which have a carboxylic acid group in the anomeric position of the reducing sugar part of the disaccharide instead of the phosphoric acid group in lipid A, is described. We investigated the influence of the substituents in the 2'- and 6'-position of the molecules synthesized on their activities toward human monoblastic U937 cells. It was revealed that a series of compounds, possessing an acetamido group in the 2'-position showed strong LPS-antagonistic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00684-0

文献信息

• Lipid A-Type Pyrancarboxylic Acid Derivatives, their Synthesis and their Biological Activities
  作者：Takashi Mochizuki、Yuji Iwano、Masao Shiozaki、Shin-ichi Kurakata、Saori Kanai、Masahiro Nishijima

  DOI：10.1016/s0040-4020(00)00684-0

  日期：2000.9

  Synthesis of lipid A-type pyrancarboxylic acid derivatives, which have a carboxylic acid group in the anomeric position of the reducing sugar part of the disaccharide instead of the phosphoric acid group in lipid A, is described. We investigated the influence of the substituents in the 2'- and 6'-position of the molecules synthesized on their activities toward human monoblastic U937 cells. It was revealed that a series of compounds, possessing an acetamido group in the 2'-position showed strong LPS-antagonistic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis and biological activities of lipid A-type pyrancarboxylic acid derivatives
  作者：Takashi Mochizuki、Yuji Iwano、Masao Shiozaki、Shin-ichi Kurakata、Saori Kanai、Masahiro Nishijima

  DOI：10.1016/s0008-6215(99)00326-2

  日期：2000.3

  The synthesis of lipid A-type pyrancarboxylic acid derivatives, which have a carboxylic acid group in the anomeric position of the reducing part of the disaccharide instead of the phosphate group in lipid A, is described. One of the compounds thus synthesized, which has an acyl substitution pattern similar to that of Escherichia coli lipid A, showed lipopolysaccharide (LPS)-agonistic activity. The other, which contains four lipid chains in the molecule, exhibited strong LPS-antagonistic activity toward human monoblastic U937 cells. (C) 2000 Elsevier Science Ltd. All rights reserved.