tert-butyl(3β)-cholestan-3-yl[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]carbamate | 906371-70-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: tert-butyl(3β)-cholestan-3-yl[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]carbamate
• CAS: 906371-70-8
• 化学式: C₄₃H₆₆N₂O₄
• 分子量: 675.008
• InChiKey: BSIGWEITAFKUPT-ZUGIMWFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  49.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  66.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl(3β)-cholestan-3-yl[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]carbamate 在 lithium hydroxide 、 N,N-二异丙基乙胺 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 N-{[(3-[(tert-butoxycarbonyl)(cholestan-3-yl)amino]propyl)amino]carbonyl}-β-alanine
  参考文献：
  名称：

  A Synthetic Mimic of Human Fc Receptors:  Defined Chemical Modification of Cell Surfaces Enables Efficient Endocytic Uptake of Human Immunoglobulin-G

  摘要：

  Binding of ligands to macromolecular receptors on the surface of mammalian cells often results in ligand uptake through receptor-mediated endocytosis. Certain human leukocytes and epithelial cells express Fc receptors (FcRs) that bind and internalize antibodies through this mechanism. To mimic this process, we synthesized an artificial FcR comprising the membrane anchor N-alkyl-3 beta-amino-5 alpha-cholestane linked to a disulfide-constrained cyclic peptide, termed FcIII, known to exhibit high affinity and specificity for the Fc region of human IgG. Treatment of human Jurkat lymphocytes that lack natural FcRs with the synthetic FcR (1 mu M, 1 h) installed an average of similar to 6.2 x 10(5) synthetic receptor molecules per cell surface. These treated cells gained the capacity to internalize human IgG at levels greater than human THP-1 cells that express the natural receptors Fc gamma RI and Fc gamma RII. By linking binding motifs for circulating ligands to membrane anchors that cycle between the cell surface and intracellular endosomes, minimalistic cell surface receptors can be used to destroy targeted ligands by endocytosis. These small mimics of macromolecular receptors may be useful for controlling the extracellular abundance of ligands involved in disease.

  DOI：

  10.1021/ja062377w
• 作为产物：
  描述：

  3β-amino-5α-cholestane 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 tert-butyl(3β)-cholestan-3-yl[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]carbamate
  参考文献：
  名称：

  A Synthetic Mimic of Human Fc Receptors:  Defined Chemical Modification of Cell Surfaces Enables Efficient Endocytic Uptake of Human Immunoglobulin-G

  摘要：

  Binding of ligands to macromolecular receptors on the surface of mammalian cells often results in ligand uptake through receptor-mediated endocytosis. Certain human leukocytes and epithelial cells express Fc receptors (FcRs) that bind and internalize antibodies through this mechanism. To mimic this process, we synthesized an artificial FcR comprising the membrane anchor N-alkyl-3 beta-amino-5 alpha-cholestane linked to a disulfide-constrained cyclic peptide, termed FcIII, known to exhibit high affinity and specificity for the Fc region of human IgG. Treatment of human Jurkat lymphocytes that lack natural FcRs with the synthetic FcR (1 mu M, 1 h) installed an average of similar to 6.2 x 10(5) synthetic receptor molecules per cell surface. These treated cells gained the capacity to internalize human IgG at levels greater than human THP-1 cells that express the natural receptors Fc gamma RI and Fc gamma RII. By linking binding motifs for circulating ligands to membrane anchors that cycle between the cell surface and intracellular endosomes, minimalistic cell surface receptors can be used to destroy targeted ligands by endocytosis. These small mimics of macromolecular receptors may be useful for controlling the extracellular abundance of ligands involved in disease.

  DOI：

  10.1021/ja062377w