Acetic acid (1S,2R)-2-acetoxy-1-((S)-2-hydroxy-1-octanoylamino-ethyl)-hexadecyl ester | 791611-39-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Acetic acid (1S,2R)-2-acetoxy-1-((S)-2-hydroxy-1-octanoylamino-ethyl)-hexadecyl ester
• 英文别名: [(2S,3S,4R)-3-acetyloxy-1-hydroxy-2-(octanoylamino)octadecan-4-yl] acetate
• CAS: 791611-39-7
• 化学式: C₃₀H₅₇NO₆
• 分子量: 527.786
• InChiKey: FERMRYDADUHGBR-LXQNXJGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  37
• 可旋转键数：
  27
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,2R)-2-acetoxy-1-((S)-2-hydroxy-1-octanoylamino-ethyl)-hexadecyl ester 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 silver trifluoromethanesulfonate 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、1.38 MPa 条件下， 反应 16.0h， 生成
  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：

  在 4-二甲氨基吡啶 、 氢氟酸 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 Acetic acid (1S,2R)-2-acetoxy-1-((S)-2-hydroxy-1-octanoylamino-ethyl)-hexadecyl 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

文献信息

• Synthesis of diglycosylceramides and evaluation of their iNKT cell stimulatory properties
  作者：Yang Liu、Shenglou Deng、Li Bai、Stefan Freigang、Jochen Mattner、Luc Teyton、Albert Bendelac、Paul B. Savage

  DOI：10.1016/j.bmcl.2007.12.067

  日期：2008.5

  Stimulation of iNKT cells is highly dependent on the structures of the glycolipids presented by CD1d. Furthermore, antigen processing and CD1d loading in lysosomes play central roles in controlling the stimulatory properties of glycolipid antigens. Previously, we determined that substitution at C6 '' on alpha-galactosylceramides did not significantly impact stimulatory properties; however, it was not known if substitution at this position influenced lysosomal processing of oligoglycosylceramides. We have prepared a series of mono- and di-galactosylceramides to observe the impact of C6 '' substitution on glycosidase truncation of these glycolipids. We found that substitution did not significantly impact glycosidase activity or loading into CD1d. (c) 2007 Elsevier Ltd. All rights reserved.