(R)-2-(t-butoxycarbonylamino)-3-(5-(diethoxyphosphoryl)-1H-1,2,3-triazol-1-yl)propanoic acid

• 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: (R)-2-(t-butoxycarbonylamino)-3-(5-(diethoxyphosphoryl)-1H-1,2,3-triazol-1-yl)propanoic acid
• 化学式: C₁₄H₂₅N₄O₇P
• 分子量: 392.349
• InChiKey: WAYPNYXJELEVKF-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  141.87
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  diethyl ethynylphosphonate 在 二(三苯基膦)环戊二烯基氯化钌(II) 、 lithium hydroxide monohydrate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 26.0h， 生成 (S)-2-(tert-butoxycarbonylamino)-3-(5-(diethoxyphosphoryl)-1H-1,2,3-triazol-1-yl)propanoic acid 、 (R)-2-(t-butoxycarbonylamino)-3-(5-(diethoxyphosphoryl)-1H-1,2,3-triazol-1-yl)propanoic acid
  参考文献：
  名称：

  Stable triazolylphosphonate analogues of phosphohistidine

  摘要：

  Histidine-phosphorylated proteins and the corresponding kinases are important components of bacterial and eukaryotic cell-signalling pathways, and are therefore potential drug targets. The study of these biomolecules has been hampered by the lability of the phosphoramidate functional group in the phosphohistidines and the lack of generic antibodies. Herein, the design and concise synthesis of stable triazolylphosphonate analogues of N1- and N3-phosphohistidine, and derivatives suitable for bioconjugation, are described.

  DOI：

  10.1007/s00726-011-1145-2

文献信息

• Stable triazolylphosphonate analogues of phosphohistidine
  作者：Shin Mukai、Gavin R. Flematti、Lindsay T. Byrne、Paul G. Besant、Paul V. Attwood、Matthew J. Piggott

  DOI：10.1007/s00726-011-1145-2

  日期：2012.8

  Histidine-phosphorylated proteins and the corresponding kinases are important components of bacterial and eukaryotic cell-signalling pathways, and are therefore potential drug targets. The study of these biomolecules has been hampered by the lability of the phosphoramidate functional group in the phosphohistidines and the lack of generic antibodies. Herein, the design and concise synthesis of stable triazolylphosphonate analogues of N1- and N3-phosphohistidine, and derivatives suitable for bioconjugation, are described.