tert-butyl N-3,6,9,12-tetraoxapentadec-14-yn-1-yl-N2-{[3,4,5-tris(acetyloxy)phenyl]carbonyl}-L-α-glutaminate | 1400658-44-7

• 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: tert-butyl N-3,6,9,12-tetraoxapentadec-14-yn-1-yl-N2-{[3,4,5-tris(acetyloxy)phenyl]carbonyl}-L-α-glutaminate
• 英文别名: tert-butyl (4S)-5-oxo-5-[2-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]ethylamino]-4-[(3,4,5-triacetyloxybenzoyl)amino]pentanoate
• CAS: 1400658-44-7
• 化学式: C₃₃H₄₆N₂O₁₄
• 分子量: 694.733
• InChiKey: QJAREBWWUXUFOV-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  49
• 可旋转键数：
  27
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  200
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  tert-butyl N-3,6,9,12-tetraoxapentadec-14-yn-1-yl-N2-{[3,4,5-tris(acetyloxy)phenyl]carbonyl}-L-α-glutaminate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.25h， 以95%的产率得到(4S)-5-oxo-5-[2-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]ethylamino]-4-[(3,4,5-triacetyloxybenzoyl)amino]pentanoic acid
  参考文献：
  名称：

  Chemical Functionalization of Bioceramics To Enhance Endothelial Cells Adhesion for Tissue Engineering

  摘要：

  To control the selective adhesion of human endothelial cells and human serum proteins to bioceramics of different compositions, a multifunctional ligand containing a cyclic arginine-glycine-aspartate (RGD) peptide, a tetraethylene glycol spacer, and a gallate moiety was designed, synthesized, and characterized. The binding of this ligand to alumina-based, hydroxyapatite-based, and calcium phosphate-based bioceramics was demonstrated. The conjugation of this ligand to the bioceramics induced a decrease in the nonselective and integrin-selective binding of human serum proteins, whereas the binding and adhesion of human endothelial cells was enhanced, dependent on the particular bioceramics.

  DOI：

  10.1021/jm301092r
• 作为产物：
  描述：

  Fmoc-O-叔丁基-L-谷氨酸 在 哌啶 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 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 1.25h， 生成 tert-butyl N-3,6,9,12-tetraoxapentadec-14-yn-1-yl-N2-{[3,4,5-tris(acetyloxy)phenyl]carbonyl}-L-α-glutaminate
  参考文献：
  名称：

  Chemical Functionalization of Bioceramics To Enhance Endothelial Cells Adhesion for Tissue Engineering

  摘要：

  To control the selective adhesion of human endothelial cells and human serum proteins to bioceramics of different compositions, a multifunctional ligand containing a cyclic arginine-glycine-aspartate (RGD) peptide, a tetraethylene glycol spacer, and a gallate moiety was designed, synthesized, and characterized. The binding of this ligand to alumina-based, hydroxyapatite-based, and calcium phosphate-based bioceramics was demonstrated. The conjugation of this ligand to the bioceramics induced a decrease in the nonselective and integrin-selective binding of human serum proteins, whereas the binding and adhesion of human endothelial cells was enhanced, dependent on the particular bioceramics.

  DOI：

  10.1021/jm301092r