(2S)-2-({(2S)-2-[(hydroxy{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}phosphoryl)amino]-4-methylpentanoyl}amino)-3-(1H-indol-3-yl)propionate disodium

• 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: (2S)-2-({(2S)-2-[(hydroxy{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}phosphoryl)amino]-4-methylpentanoyl}amino)-3-(1H-indol-3-yl)propionate disodium
• 英文别名: N-(α-rhamnopyranosyloxyhydroxyphosphinyl)-L-leucyl-L-tryptophan disodium；phosphoramidon disodium salt；phosphoramidon disodium；phosphoramidon；sodium;(2S)-3-(1H-indol-3-yl)-2-[[(2S)-4-methyl-2-[[oxido-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphosphoryl]amino]pentanoyl]amino]propanoate
• 化学式: C₂₃H₃₂N₃O₁₀P*2Na
• 分子量: 587.474
• InChiKey: IFGCUJZIWBUILZ-KGUNCBEVSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -4.73
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  216
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  L-rhamnopyranose 在 5%-palladium/activated carbon 、 氢气 、 sodium methylate 、 sodium acetate 、 溶剂黄146 、 乙二胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 35.5h， 生成 (2S)-2-({(2S)-2-[(hydroxy{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}phosphoryl)amino]-4-methylpentanoyl}amino)-3-(1H-indol-3-yl)propionate disodium
  参考文献：
  名称：

  Synthesis and enzymatic evaluation of phosphoramidon and its β anomer: Anomerization of α-l-rhamnose triacetate upon phosphitylation

  摘要：

  A novel and efficient strategy for the synthesis of phosphoramidon and its beta anomer has been developed by manipulating the anomerization of alpha-L-rhamnose triacetate upon phosphitylation. The experimental results suggest that proton transfer, bond rotation, and N atom are the key factors for the anomerization. The determined K-i and K-d values establish that phosphoramidon prepared by this method possesses excellent biological activity, and indicate that the contacts of rhamnose moiety with the enzyme have limited contribution to the binding. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.052