ammonium dimethyl phosphate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: ammonium dimethyl phosphate
• 英文别名: Ammonium dimethylphosphate；azanium;dimethyl phosphate
• 化学式: C₂H₇O₄P*H₃N
• 分子量: 143.079
• InChiKey: ORCKRXIGKKZTAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.12
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  59.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  磷酸三甲酯 在 ammonium hydroxide 作用下， 生成 ammonium dimethyl phosphate
  参考文献：
  名称：

  Synthesis of (S)-Isoprenoid Thiodiphosphates as Substrates and Inhibitors

  摘要：

  Thiolo thiophosphate analogues of isopentenyl diphosphate (IPP), dimethylallyl. diphosphate (DMAPP), geranyl diphosphate (GPP), farnesyl diphosphate (FPP), and geranylgeranyl diphosphate (GGPP) were synthesized, Inorganic thiopyrophosphate (SPP) was prepared from trimethyl phosphate in four steps. The tris(tetra-n-butylammonium) salt was then used to convert isopentenyl tosylate to (S)-isopentenyl thiodiphosphate (ISPP). (S)-Dimethylallyl (DMASPP), (S)-geranyl (GSPP), (S)-farnesyl (FSPP), and (S)-geranylgeranyl thiodiphosphate (GGSPP) were prepared from the corresponding bromides in a similar manner. ISPP and GSPP were substrates for avian farnesyl diphosphate synthase (FPPase). Incubation of the enzyme with ISPP and GPP gave FSPP, whereas incubation with IPP and GSPP gave FPP. GSPP was a substantially less reactive than GPP in the chain elongation reaction and was an excellent competitive inhibitor, K-I(GSPP) = 24.8 muM, of the enzyme. Thus, when ISPP and DMAPP were incubated with FPPase, GSPP accumulated and was only slowly converted to FSPP.

  DOI：

  10.1021/jo010505n

文献信息

• Synthesis of (<i>S</i>)-Isoprenoid Thiodiphosphates as Substrates and Inhibitors
  作者：Richard M. Phan、C. Dale Poulter

  DOI：10.1021/jo010505n

  日期：2001.10.1

  Thiolo thiophosphate analogues of isopentenyl diphosphate (IPP), dimethylallyl. diphosphate (DMAPP), geranyl diphosphate (GPP), farnesyl diphosphate (FPP), and geranylgeranyl diphosphate (GGPP) were synthesized, Inorganic thiopyrophosphate (SPP) was prepared from trimethyl phosphate in four steps. The tris(tetra-n-butylammonium) salt was then used to convert isopentenyl tosylate to (S)-isopentenyl thiodiphosphate (ISPP). (S)-Dimethylallyl (DMASPP), (S)-geranyl (GSPP), (S)-farnesyl (FSPP), and (S)-geranylgeranyl thiodiphosphate (GGSPP) were prepared from the corresponding bromides in a similar manner. ISPP and GSPP were substrates for avian farnesyl diphosphate synthase (FPPase). Incubation of the enzyme with ISPP and GPP gave FSPP, whereas incubation with IPP and GSPP gave FPP. GSPP was a substantially less reactive than GPP in the chain elongation reaction and was an excellent competitive inhibitor, K-I(GSPP) = 24.8 muM, of the enzyme. Thus, when ISPP and DMAPP were incubated with FPPase, GSPP accumulated and was only slowly converted to FSPP.