2-deoxy-6-O-(2-deoxy-3-O-((R)-3-hydroxytetradecanoyl)-2-((R)-3-hydroxytetradecanoylamino)-β-D-glucopyranosyl)-3-O-((R)-3-hydroxytetradecanoyl)-2-((R)-3-hydroxytetradecanoylamino)-α-D-glucopyranose 1,4'-bisphosphate | 91841-27-9

• 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-3-O-((R)-3-hydroxytetradecanoyl)-2-((R)-3-hydroxytetradecanoylamino)-β-D-glucopyranosyl)-3-O-((R)-3-hydroxytetradecanoyl)-2-((R)-3-hydroxytetradecanoylamino)-α-D-glucopyranose 1,4'-bisphosphate
• 英文别名: 2-deoxy-6-O-(2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-4-O-phosphono-β-D-glucopyranosyl)-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxyletradecanoyl]amino}-1-O-phosphono-α-D-glucopyranose；Lipid IVA；[(2R,3S,4R,5R,6R)-3-hydroxy-2-[[(2R,3R,4R,5S,6R)-6-(hydroxymethyl)-3-[[(3R)-3-hydroxytetradecanoyl]amino]-4-[(3R)-3-hydroxytetradecanoyl]oxy-5-phosphonooxyoxan-2-yl]oxymethyl]-5-[[(3R)-3-hydroxytetradecanoyl]amino]-6-phosphonooxyoxan-4-yl] (3R)-3-hydroxytetradecanoate
• CAS: 91841-27-9
• 化学式: C₆₈H₁₃₀N₂O₂₃P₂
• 分子量: 1405.73
• InChiKey: KVJWZTLXIROHIL-QDORLFPLSA-N

物化性质

• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.4
• 重原子数：
  95
• 可旋转键数：
  62
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  393
• 氢给体数：
  12
• 氢受体数：
  23

反应信息

• 作为产物：
  描述：

  C₁₃₈H₁₉₀N₂O₂₃P₂ 在 氢气 、 palladium(II) hydroxide 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-deoxy-6-O-(2-deoxy-3-O-((R)-3-hydroxytetradecanoyl)-2-((R)-3-hydroxytetradecanoylamino)-β-D-glucopyranosyl)-3-O-((R)-3-hydroxytetradecanoyl)-2-((R)-3-hydroxytetradecanoylamino)-α-D-glucopyranose 1,4'-bisphosphate
  参考文献：
  名称：

  [EN] METHOD FOR TREATING AMYLOIDOGENIC DISEASE
  [FR] MÉTHODE DE TRAITEMENT D'UNE MALADIE AMYLOÏDOGÉNIQUE

  摘要：

  公开号：

  WO2022104088A3

文献信息

• Chemical Synthesis of a Biosynthetic Precursor of Lipid A with a Phosphorylated Tetraacyl Disaccharide Structure
  作者：Masahiro Imoto、Hiroyuki Yoshimura、Michiharu Yamamoto、Tetsuo Shimamoto、Shoichi Kusumoto、Tetsuo Shiba

  DOI：10.1246/bcsj.60.2197

  日期：1987.6

  2,2′-N:3,3′-O-Tetrakis[(R)-3-hydroxytetradecanoyl]-β(1-6)-D-glucosamine disaccharide 1,4′-bis(phosphate) and its dephospho derivatives were synthesized. The bisphosphate prepared was shown to be identical with a natural biosynthetic precursor of lipid A which corresponds to the lipophilic part of lipopolysaccharide (LPS) in bacterial cell wall. The synthetic bis- and monophosphates exhibited many of

  2,2'-N:3,3'-O-Tetrakis[(R)-3-羟基十四烷酰基]-β(1-6)-D-葡糖胺二糖 1,4'-双(磷酸)及其脱磷衍生物合成的。制备的二磷酸盐显示与脂质 A 的天然生物合成前体相同，脂质 A 对应于细菌细胞壁中脂多糖 (LPS) 的亲脂部分。合成的双磷酸盐和单磷酸盐表现出 LPS 的许多典型内毒活性。因此，这项工作建立了脂质 A 生物合成前体的化学结构，并阐明了表达这些活性所需的基本结构。
• Chemical synthesis of phosphorylated tetraacyl disaccharide corresponding to a biosynthetic precursor of lipid A
  作者：M. Imoto、H. Yoshimura、M. Yamamoto、T. Shimamoto、S. Kusumoto、T. Shiba

  DOI：10.1016/s0040-4039(01)81258-2

  日期：1984.1

  A total synthesis of 2,2′-N; 3,3′-O-tetraquis[(R)-3-hydroxytetradecanoyl]-β(1–6)-D-glucosamine disaccharide 1,4′-diphosphate is described. This is the first confirmation of the fundamental structure of lipid A since the synthetic compound exhibited most of the characteristic biological activities of natural endotoxin.

  共合成2,2'-N; 描述了3,3'-O-四quis [（R）-3-羟基十四烷酰基]-β（1-6）-D-葡糖胺二糖1,4'-二磷酸酯。这是脂质A基本结构的首次确认，因为合成化合物显示出天然内毒素的大多数特征性生物活性。
• New Efficient Synthesis of a Biosynthetic Precursor of Lipid A
  作者：Masato Oikawa、Akira Wada、Hiroaki Yoshizaki、Koichi Fukase、Shoichi Kusumoto

  DOI：10.1246/bcsj.70.1435

  日期：1997.6

  A biosynthetic precursor of lipid A has been synthesized by an improved efficient method. Two appropriately modified acyl-substituted glucosamine units were synthesized from D-glucosamine using (R)-3-(benzyloxy)tetradecanoic acid and then coupled by the Lewis acid-promoted glycosidation via the corresponding trichloroacetimidate. Glycosyl phosphorylation and hydrogenolytic deprotection, followed by

  脂质 A 的生物合成前体已通过改进的有效方法合成。使用 (R)-3-(苄氧基)十四烷酸从 D-葡糖胺合成两个适当修饰的酰基取代的葡糖胺单元，然后通过路易斯酸促进的糖苷化通过相应的三氯乙酰亚胺进行偶联。糖基磷酸化和氢解脱保护，然后通过液-液分配色谱纯化，通过 13 个步骤从 N-Troc-D-葡糖胺以 2.9% 的总收率得到目标化合物。
• Disaccharide derivatives
  申请人：DAIICHI SEIYAKU CO., LTD.

  公开号：EP0172581B1

  公开（公告）日：1992-05-06
• US5066794A
  申请人：——

  公开号：US5066794A

  公开（公告）日：1991-11-19