Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-acetylamino-octadecyloxy)-tetrahydro-pyran-4-yl ester | 791611-44-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-acetylamino-octadecyloxy)-tetrahydro-pyran-4-yl ester
• CAS: 791611-44-4
• 化学式: C₄₃H₆₇NO₁₄
• 分子量: 822.003
• InChiKey: SEIWTEUJUHFEEN-LHSQPEFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  58.0
• 可旋转键数：
  28.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  188.29
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-acetylamino-octadecyloxy)-tetrahydro-pyran-4-yl ester 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、1.38 MPa 条件下， 反应 20.0h， 生成 N-[(1S,2S,3R)-2,3-Dihydroxy-1-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadecyl]-acetamide
  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：

  1,3,4,6-Tetra-O-acetyl-2-O-benzyl-D-galactopyranose 在 4 A molecular sieve 、 氢溴酸 、 silver trifluoromethanesulfonate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-acetylamino-octadecyloxy)-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