[(2R,3S,4S,5R,6S)-3,4-diacetyloxy-6-[(2S,3S,4R)-3,4-diacetyloxy-2-(tetracosanoylamino)hexoxy]-5-phenylmethoxyoxan-2-yl]methyl acetate | 791611-41-1

• 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: [(2R,3S,4S,5R,6S)-3,4-diacetyloxy-6-[(2S,3S,4R)-3,4-diacetyloxy-2-(tetracosanoylamino)hexoxy]-5-phenylmethoxyoxan-2-yl]methyl acetate
• CAS: 791611-41-1
• 化学式: C₅₃H₈₇NO₁₄
• 分子量: 962.272
• InChiKey: HZQNZDTZVJFBQN-RCHJBDRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  68
• 可旋转键数：
  43
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  188
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6S)-3,4-diacetyloxy-6-[(2S,3S,4R)-3,4-diacetyloxy-2-(tetracosanoylamino)hexoxy]-5-phenylmethoxyoxan-2-yl]methyl acetate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、1.38 MPa 条件下， 反应 12.0h， 生成 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4R)-3,4-diacetoxy-2-tetracosanoylamino-hexyloxy)-5-hydroxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Effects of Lipid Chain Lengths in α-Galactosylceramides on Cytokine Release by Natural Killer T Cells

  摘要：

  Glycolipid presentation by CD1 proteins has emerged as an important aspect of antigen recognition, and presentation of alpha-glycosylceramides by CD1d to natural killer T cells has become a central focus in understanding how glycolipid presentation can influence immune responses. An alpha-galactosylceramide containing relatively long lipid chains has been the subject of intense study because, when presented by CD1d to natural killer T cells, it stimulates the release of both proinflammatory and immunomodulatory cytokines. Using an efficient synthesis of alpha-galactosylceramides, we have prepared a series of glycolipids in which the lipid chain lengths have been incrementally varied. The responses of natural killer T cells to these glycolipids have been determined, and we have found that truncation of the phytosphingosine lipid chain increases the relative amounts of immunomodulatory cytokines released. In similar fashion, the length of the acyl chain in alpha-galactosylceramides influences cytokine release profiles.

  DOI：

  10.1021/ja045385q
• 作为产物：
  描述：

  1,-脱水-3,-O-异丙二烯-β-D-谷氨酸五乙酸酯 在 4 A molecular sieve 、 氢溴酸 、 silver trifluoromethanesulfonate 、 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 [(2R,3S,4S,5R,6S)-3,4-diacetyloxy-6-[(2S,3S,4R)-3,4-diacetyloxy-2-(tetracosanoylamino)hexoxy]-5-phenylmethoxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  Effects of Lipid Chain Lengths in α-Galactosylceramides on Cytokine Release by Natural Killer T Cells

  摘要：

  Glycolipid presentation by CD1 proteins has emerged as an important aspect of antigen recognition, and presentation of alpha-glycosylceramides by CD1d to natural killer T cells has become a central focus in understanding how glycolipid presentation can influence immune responses. An alpha-galactosylceramide containing relatively long lipid chains has been the subject of intense study because, when presented by CD1d to natural killer T cells, it stimulates the release of both proinflammatory and immunomodulatory cytokines. Using an efficient synthesis of alpha-galactosylceramides, we have prepared a series of glycolipids in which the lipid chain lengths have been incrementally varied. The responses of natural killer T cells to these glycolipids have been determined, and we have found that truncation of the phytosphingosine lipid chain increases the relative amounts of immunomodulatory cytokines released. In similar fashion, the length of the acyl chain in alpha-galactosylceramides influences cytokine release profiles.

  DOI：

  10.1021/ja045385q