Tert-butyl 3-[2-[(2-bromo-2,2-dideuterioacetyl)amino]-3-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]-2-[[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]methyl]propoxy]propanoate | 1422726-52-0

• 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 3-[2-[(2-bromo-2,2-dideuterioacetyl)amino]-3-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]-2-[[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]methyl]propoxy]propanoate
• 英文别名: tert-butyl 3-[2-[(2-bromo-2,2-dideuterioacetyl)amino]-3-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]-2-[[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]methyl]propoxy]propanoate
• CAS: 1422726-52-0
• 化学式: C₂₇H₄₈BrNO₁₀
• 分子量: 628.567
• InChiKey: SKCOMTBIMRIDIZ-BPPAMHLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  39
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tris[8-carboxy-2,2,6,6-(²H₃-tetramethyl)benzo[1,2-d:4,5-d′]bis-([1,3]dithiole)-4-yl]methyl radical 、 Tert-butyl 3-[2-[(2-bromo-2,2-dideuterioacetyl)amino]-3-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]-2-[[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]methyl]propoxy]propanoate 在 potassium carbonate 作用下， 以 氘代二甲亚砜 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Esterified Dendritic TAM Radicals with Very High Stability and Enhanced Oxygen Sensitivity

  摘要：

  In this work, we have developed a new class of dendritic TAM radicals (TG, TdG, and dTdG) through a convergent method based on the TAM core CT-03 or its deuterated analogue dCT-03 and trifurcated Newkome-type monomer. Among these radicals, dTdG exhibits the best EPR properties with sharpest EPR singlet and highest O-2 sensitivity due to deuteration of both the ester linker groups and the TAM core CT-03. Like the previous dendritic TAM radicals, these new compounds also show extremely high stability toward various reactive species owing to the dendritic encapsulation. The highly charged nature of these molecules resulting from nine carboxylate groups prevents concentration-dependent EPR line broadening at physiological pH. Furthermore, we demonstrate that these TAM radicals can be easily derivatized (e.g., PEGylation) at the nine carboxylate groups and the resulting PEGylated analogue dTdG PEG completely inhibits the albumin binding, thereby enhancing suitability for in vivo applications. These new dendritic TAM radicals show great potential for in vivo EPR oximetric applications and provide insights on approaches to develop improved and targeted EPR oximetric probes for biomedical applications.

  DOI：

  10.1021/jo301849k
• 作为产物：
  描述：

  bromoacetic-2,2-d2 acid bromoanhydride 、 三[[2-(叔-丁氧羰基)乙氧基]甲基]甲胺 在 potassium carbonate 作用下， 以 氘代氯仿 为溶剂， 反应 1.5h， 以80%的产率得到Tert-butyl 3-[2-[(2-bromo-2,2-dideuterioacetyl)amino]-3-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]-2-[[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]methyl]propoxy]propanoate
  参考文献：
  名称：

  Esterified Dendritic TAM Radicals with Very High Stability and Enhanced Oxygen Sensitivity

  摘要：

  In this work, we have developed a new class of dendritic TAM radicals (TG, TdG, and dTdG) through a convergent method based on the TAM core CT-03 or its deuterated analogue dCT-03 and trifurcated Newkome-type monomer. Among these radicals, dTdG exhibits the best EPR properties with sharpest EPR singlet and highest O-2 sensitivity due to deuteration of both the ester linker groups and the TAM core CT-03. Like the previous dendritic TAM radicals, these new compounds also show extremely high stability toward various reactive species owing to the dendritic encapsulation. The highly charged nature of these molecules resulting from nine carboxylate groups prevents concentration-dependent EPR line broadening at physiological pH. Furthermore, we demonstrate that these TAM radicals can be easily derivatized (e.g., PEGylation) at the nine carboxylate groups and the resulting PEGylated analogue dTdG PEG completely inhibits the albumin binding, thereby enhancing suitability for in vivo applications. These new dendritic TAM radicals show great potential for in vivo EPR oximetric applications and provide insights on approaches to develop improved and targeted EPR oximetric probes for biomedical applications.

  DOI：

  10.1021/jo301849k

文献信息

• Esterified Dendritic TAM Radicals with Very High Stability and Enhanced Oxygen Sensitivity
  作者：Yuguang Song、Yangping Liu、Craig Hemann、Frederick A. Villamena、Jay L. Zweier

  DOI：10.1021/jo301849k

  日期：2013.2.15

  In this work, we have developed a new class of dendritic TAM radicals (TG, TdG, and dTdG) through a convergent method based on the TAM core CT-03 or its deuterated analogue dCT-03 and trifurcated Newkome-type monomer. Among these radicals, dTdG exhibits the best EPR properties with sharpest EPR singlet and highest O-2 sensitivity due to deuteration of both the ester linker groups and the TAM core CT-03. Like the previous dendritic TAM radicals, these new compounds also show extremely high stability toward various reactive species owing to the dendritic encapsulation. The highly charged nature of these molecules resulting from nine carboxylate groups prevents concentration-dependent EPR line broadening at physiological pH. Furthermore, we demonstrate that these TAM radicals can be easily derivatized (e.g., PEGylation) at the nine carboxylate groups and the resulting PEGylated analogue dTdG PEG completely inhibits the albumin binding, thereby enhancing suitability for in vivo applications. These new dendritic TAM radicals show great potential for in vivo EPR oximetric applications and provide insights on approaches to develop improved and targeted EPR oximetric probes for biomedical applications.