12-<6-(biotinoylamino)hexanoylamino>dodecanoic acid | 223733-86-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: 12-<6-(biotinoylamino)hexanoylamino>dodecanoic acid
• 英文别名: 12-[6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]hexanoylamino]dodecanoic acid
• CAS: 223733-86-6
• 化学式: C₂₈H₅₀N₄O₅S
• 分子量: 554.795
• InChiKey: OJLLUWZPHFWZSW-WCYRKSIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  38
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  162
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-1-O-(α-D-galactopyranosyl)-1,3,4-octadecanetriol 、 12-<6-(biotinoylamino)hexanoylamino>dodecanoic acid 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (2S,3S,4R)-1-O-(α-D-galactopyranosyl)-2--1,3,4-octadecanetriol
  参考文献：
  名称：

  Syntheses of Biotinylated α-Galactosylceramides and Their Effects on the Immune System and CD1 Molecules

  摘要：

  A representative alpha-galactosylceramide (alpha-GalCer), KRN7000, has strong immunostimulatory and antitumor activity. Recent studies demonstrated that KRN7000-pulsed antigen-presenting cells (APC) can activate natural killer T (NKT) cells, a novel T-cell lineage, and CD1d molecules on APC play an important role in the activation of NKT cells. However, it remains unclear whether alpha-GalCers actually bind to CD1d molecules. To address this question, we synthesized three kinds of biotinylated alpha-GalCer and a biotinylated beta-GalCer and found that the biotinylated alpha-GalCers significantly stimulate the proliferation of murine spleen cells, but the biotinylated beta-GalCer does not and that all biotinylated compounds bind to CD1d molecules.

  DOI：

  10.1021/jm990054n
• 作为产物：
  描述：

  N-生物素己酸 在 sodium hydroxide 、 WSC*HCl 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 12-<6-(biotinoylamino)hexanoylamino>dodecanoic acid
  参考文献：
  名称：

  Syntheses of Biotinylated α-Galactosylceramides and Their Effects on the Immune System and CD1 Molecules

  摘要：

  A representative alpha-galactosylceramide (alpha-GalCer), KRN7000, has strong immunostimulatory and antitumor activity. Recent studies demonstrated that KRN7000-pulsed antigen-presenting cells (APC) can activate natural killer T (NKT) cells, a novel T-cell lineage, and CD1d molecules on APC play an important role in the activation of NKT cells. However, it remains unclear whether alpha-GalCers actually bind to CD1d molecules. To address this question, we synthesized three kinds of biotinylated alpha-GalCer and a biotinylated beta-GalCer and found that the biotinylated alpha-GalCers significantly stimulate the proliferation of murine spleen cells, but the biotinylated beta-GalCer does not and that all biotinylated compounds bind to CD1d molecules.

  DOI：

  10.1021/jm990054n

文献信息

• Syntheses of Biotinylated α-Galactosylceramides and Their Effects on the Immune System and CD1 Molecules
  作者：Teruyuki Sakai、Olga V. Naidenko、Hirosi Iijima、Mitchell Kronenberg、Yasuhiko Koezuka

  DOI：10.1021/jm990054n

  日期：1999.5.1

  A representative alpha-galactosylceramide (alpha-GalCer), KRN7000, has strong immunostimulatory and antitumor activity. Recent studies demonstrated that KRN7000-pulsed antigen-presenting cells (APC) can activate natural killer T (NKT) cells, a novel T-cell lineage, and CD1d molecules on APC play an important role in the activation of NKT cells. However, it remains unclear whether alpha-GalCers actually bind to CD1d molecules. To address this question, we synthesized three kinds of biotinylated alpha-GalCer and a biotinylated beta-GalCer and found that the biotinylated alpha-GalCers significantly stimulate the proliferation of murine spleen cells, but the biotinylated beta-GalCer does not and that all biotinylated compounds bind to CD1d molecules.