6-O-{2-deoxy-2-[(R)-3-hexadecanoyloxy-15-methylhexadecanoylamino]-3-O-[(R)-3-hydroxy-13-methyltetradecanoylamino]-β-D-glucopyranosyl}-2-deoxy-2-[(R)-3-hydroxy-15-methylhexadecanoylamino]-α-D-glucopyranose 1-phosphate | 940892-73-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-{2-deoxy-2-[(R)-3-hexadecanoyloxy-15-methylhexadecanoylamino]-3-O-[(R)-3-hydroxy-13-methyltetradecanoylamino]-β-D-glucopyranosyl}-2-deoxy-2-[(R)-3-hydroxy-15-methylhexadecanoylamino]-α-D-glucopyranose 1-phosphate
• 英文别名: [(3R)-1-[[(2R,3R,4R,5S,6R)-2-[[(2R,3S,4R,5R,6R)-3,4-dihydroxy-5-[[(3R)-3-hydroxy-15-methylhexadecanoyl]amino]-6-phosphonooxyoxan-2-yl]methoxy]-5-hydroxy-6-(hydroxymethyl)-4-[(3R)-3-hydroxy-13-methyltetradecanoyl]oxyoxan-3-yl]amino]-15-methyl-1-oxohexadecan-3-yl] hexadecanoate
• CAS: 940892-73-9
• 化学式: C₇₇H₁₄₇N₂O₁₉P
• 分子量: 1435.99
• InChiKey: UADBSWOFGAVWDL-FSDYSABGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.8
• 重原子数：
  99
• 可旋转键数：
  66
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  327
• 氢给体数：
  10
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  在 氢气 、 钯 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 以76%的产率得到6-O-{2-deoxy-2-[(R)-3-hexadecanoyloxy-15-methylhexadecanoylamino]-3-O-[(R)-3-hydroxy-13-methyltetradecanoylamino]-β-D-glucopyranosyl}-2-deoxy-2-[(R)-3-hydroxy-15-methylhexadecanoylamino]-α-D-glucopyranose 1-phosphate
  参考文献：
  名称：

  Synthetic tetra-acylated derivatives of lipid A from Porphyromonas gingivalis are antagonists of human TLR4

  摘要：

  来自牙龈卟啉单胞菌LPS的四酰化脂质A已通过使用关键的二糖中间体合成，该中间体功能化带有乙酰丙酸酯（Lev）、烯丙氧基碳酸酯（Alloc）和异头二甲基苯基硅烷（TDS）作为正交保护基团，以及9-芴甲氧基羰酰胺（Fmoc）和叠氮基作为氨基保护基团。此外，已采用高效的交叉复分解反应制备了牙龈卟啉单胞菌脂质A中不寻常的分支R-(3)-羟基-13-甲基十四烷酸和(R)-3-十六烷酰氧基-15-甲基十六烷酸。生物学研究显示，合成脂质A不能激活人体和小鼠的TLR2和TLR4以产生细胞因子。然而，研究发现这些化合物是肠道LPS诱导的人单核细胞分泌细胞因子的强效拮抗剂。

  DOI：

  10.1039/b809090d

文献信息

• Synthetic tetra-acylated derivatives of lipid A from Porphyromonas gingivalis are antagonists of human TLR4
  作者：Yanghui Zhang、Jidnyasa Gaekwad、Margreet A. Wolfert、Geert-Jan Boons

  DOI：10.1039/b809090d

  日期：——

  Tetra-acylated lipid As derived from Porphyromonas gingivalis LPS have been synthesized using a key disaccharide intermediate functionalized with levulinate (Lev), allyloxycarbonate (Alloc) and anomeric dimethylthexylsilyl (TDS) as orthogonal protecting groups and 9-fluorenylmethoxycarbamate (Fmoc) and azido as amino protecting groups. Furthermore, an efficient cross-metathesis has been employed for the preparation of the unusual branched R-(3)-hydroxy-13-methyltetradecanic acid and (R)-3-hexadecanoyloxy-15-methylhexadecanoic acid of P. gingivalislipid A. Biological studies have shown that the synthetic lipid As cannot activate human and mouse TLR2 and TLR4 to produce cytokines. However, it has been found that the compounds are potent antagonist of cytokine secretion by human monocytic cells induced by enteric LPS.

  来自牙龈卟啉单胞菌LPS的四酰化脂质A已通过使用关键的二糖中间体合成，该中间体功能化带有乙酰丙酸酯（Lev）、烯丙氧基碳酸酯（Alloc）和异头二甲基苯基硅烷（TDS）作为正交保护基团，以及9-芴甲氧基羰酰胺（Fmoc）和叠氮基作为氨基保护基团。此外，已采用高效的交叉复分解反应制备了牙龈卟啉单胞菌脂质A中不寻常的分支R-(3)-羟基-13-甲基十四烷酸和(R)-3-十六烷酰氧基-15-甲基十六烷酸。生物学研究显示，合成脂质A不能激活人体和小鼠的TLR2和TLR4以产生细胞因子。然而，研究发现这些化合物是肠道LPS诱导的人单核细胞分泌细胞因子的强效拮抗剂。