N,N-bis(phosphonomethyl)-2-amino-2-methylpropionic acid | 120412-11-5

• 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: N,N-bis(phosphonomethyl)-2-amino-2-methylpropionic acid
• 英文别名: 2-[Bis(phosphonomethyl)amino]-2-methylpropanoic acid
• CAS: 120412-11-5
• 化学式: C₆H₁₅NO₈P₂
• 分子量: 291.135
• InChiKey: ZIVUCUJTIPERPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  156
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 2-甲基丙氨酸 在 水 、 亚磷酸二乙酯 作用下， 以52%的产率得到N,N-bis(phosphonomethyl)-2-amino-2-methylpropionic acid
  参考文献：
  名称：

  A one step/one pot synthesis of N,N-bis(phosphonomethyl)amino acids and their effects on adipogenic and osteogenic differentiation of human mesenchymal stem cells

  摘要：

  The one pot reaction of amino acids with diethylphosphite and formaldehyde yielded N,N-bis(phosphonomethyl)amino acids. This synthetic route does not require harsh reagents to cleave the ester group. The molecular structures of the new compounds were determined by X-ray diffraction methods. By employing DFT calculations the hydrolysis of the intermediate phosphonic esters to the respective acids could be explained by the decreasing P-OEt bond strength for C-alpha-bisalkylated amino acids. Biological evaluation on the adipogenic and osteogenic differentiation of mesenchymal stem cells revealed no modi. cation of the adipocyte differentiation, but inhibition of osteoblast formation at concentrations without detectable cytotoxicity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.039

文献信息

• A one step/one pot synthesis of N,N-bis(phosphonomethyl)amino acids and their effects on adipogenic and osteogenic differentiation of human mesenchymal stem cells
  作者：Johanna Kasser、Alexey A. Nazarov、Christian G. Hartinger、Brigitte Wdziekonski、Christian Dani、Maxim L. Kuznetsov、Vladimir B. Arion、Bernhard K. Keppler

  DOI：10.1016/j.bmc.2009.03.039

  日期：2009.5

  The one pot reaction of amino acids with diethylphosphite and formaldehyde yielded N,N-bis(phosphonomethyl)amino acids. This synthetic route does not require harsh reagents to cleave the ester group. The molecular structures of the new compounds were determined by X-ray diffraction methods. By employing DFT calculations the hydrolysis of the intermediate phosphonic esters to the respective acids could be explained by the decreasing P-OEt bond strength for C-alpha-bisalkylated amino acids. Biological evaluation on the adipogenic and osteogenic differentiation of mesenchymal stem cells revealed no modi. cation of the adipocyte differentiation, but inhibition of osteoblast formation at concentrations without detectable cytotoxicity. (C) 2009 Elsevier Ltd. All rights reserved.