6-O-phosphocholine-β-D-galactopyranosyl-(1->6)-β-D-galactopyranosyl-(1->1)-(2S,3R,4E)-2-hexadecanamido-4-octadecene-1,3-diol | 1063697-84-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: 6-O-phosphocholine-β-D-galactopyranosyl-(1->6)-β-D-galactopyranosyl-(1->1)-(2S,3R,4E)-2-hexadecanamido-4-octadecene-1,3-diol
• 英文别名: [(2R,3R,4S,5R,6R)-6-[[(2R,3R,4S,5R,6R)-6-[(E,2S,3R)-2-(hexadecanoylamino)-3-hydroxyoctadec-4-enoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 1063697-84-6
• 化学式: C₅₁H₉₉N₂O₁₆P
• 分子量: 1027.32
• InChiKey: XVXXLODTTDCPSI-RVCKBHRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  70
• 可旋转键数：
  42
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  266
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  2,3,4-tri-O-benzoyl-6-O-phosphocholine-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->1)-(2S,3R,4E)-3-O-benzoyl-2-hexadecanamido-4-octadecene-1,3-diol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以62%的产率得到6-O-phosphocholine-β-D-galactopyranosyl-(1->6)-β-D-galactopyranosyl-(1->1)-(2S,3R,4E)-2-hexadecanamido-4-octadecene-1,3-diol
  参考文献：
  名称：

  Synthetic studies on glycosphingolipids from Protostomia phyla: syntheses and biological activities of amphoteric glycolipids containing a phosphocholine residue from the earthworm Pheretima hilgendorfi

  摘要：

  Two types of amphoteric glycosphingolipid found in the earthworm Pheretima hilgendorfi, PC(-> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 1)Cer (1) and PC(-> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 1)Cer (2), and their derivatives (4, 5) were synthesized. These were examined for their ability to enhance production of interleukin-8 (IL-8), a potent inflammatory cytokine involved in neutrophil chemotaxis, in a TNF alpha-stimulated granulocytic HL-60 cells. Compounds 1 and 2 were found to be potent enhancers of IL-8 production. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.05.001

文献信息

• Synthetic studies on glycosphingolipids from Protostomia phyla: syntheses and biological activities of amphoteric glycolipids containing a phosphocholine residue from the earthworm Pheretima hilgendorfi
  作者：Noriyasu Hada、Yukihiko Shida、Hiroshi Shimamura、Yoshiko Sonoda、Tadashi Kasahara、Mutsumi Sugita、Tadahiro Takeda

  DOI：10.1016/j.carres.2008.05.001

  日期：2008.9

  Two types of amphoteric glycosphingolipid found in the earthworm Pheretima hilgendorfi, PC(-> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 1)Cer (1) and PC(-> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 1)Cer (2), and their derivatives (4, 5) were synthesized. These were examined for their ability to enhance production of interleukin-8 (IL-8), a potent inflammatory cytokine involved in neutrophil chemotaxis, in a TNF alpha-stimulated granulocytic HL-60 cells. Compounds 1 and 2 were found to be potent enhancers of IL-8 production. (C) 2008 Elsevier Ltd. All rights reserved.