3-(2,6-diaminopyrimidin-4-ylcarbamoyl)propanoic acid | 1422426-90-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(2,6-diaminopyrimidin-4-ylcarbamoyl)propanoic acid
• 英文别名: TAPAS；4-((2,6-Diaminopyrimidin-4-yl)amino)-4-oxobutanoic acid；4-[(2,6-diaminopyrimidin-4-yl)amino]-4-oxobutanoic acid
• CAS: 1422426-90-1
• 化学式: C₈H₁₁N₅O₃
• 分子量: 225.207
• InChiKey: FRMWLIAEIWMKFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(2,6-diaminopyrimidin-4-ylcarbamoyl)propanoic acid 在 sodium hydroxide 作用下， 反应 4.0h， 生成 2,4,6-三氨基嘧啶
  参考文献：
  名称：

  Efficient Self-Assembly in Water of Long Noncovalent Polymers by Nucleobase Analogues

  摘要：

  Molecular self-assembly is widely appreciated to result from a delicate balance between several noncovalent interactions and solvation effects. However, current design approaches for achieving self-assembly in water with small, synthetic molecules do not consider all aspects of the hydrophobic effect, in particular the requirement of surface areas greater than 1 nm(2) for an appreciable free energy of hydration. With the concept of a minimum hydrophobic surface area in mind, we designed a system that achieves highly cooperative self-assembly in water. Two weakly interacting low-molecular-weight monomers (cyanuric acid and a modified triaminopyrimidine) are shown to form extremely long supramolecular polymer assemblies that retain water solubility. The complete absence of intermediate assemblies means that the observed equilibrium is between free monomers and supramolecular assemblies. These observations are in excellent agreement with literature values for the free energy of nucleic acid base interactions as well as the calculated free energy penalty for the exposure of hydrophobic structures in water. The results of our study have implications for the design of new self-assembling structures and hydrogel-forming molecules and may provide insights into the origin of the first RNA-like polymers.

  DOI：

  10.1021/ja312155v
• 作为产物：
  描述：

  丁二酸酐 、 2,4,6-三氨基嘧啶 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以52%的产率得到3-(2,6-diaminopyrimidin-4-ylcarbamoyl)propanoic acid
  参考文献：
  名称：

  Efficient Self-Assembly in Water of Long Noncovalent Polymers by Nucleobase Analogues

  摘要：

  Molecular self-assembly is widely appreciated to result from a delicate balance between several noncovalent interactions and solvation effects. However, current design approaches for achieving self-assembly in water with small, synthetic molecules do not consider all aspects of the hydrophobic effect, in particular the requirement of surface areas greater than 1 nm(2) for an appreciable free energy of hydration. With the concept of a minimum hydrophobic surface area in mind, we designed a system that achieves highly cooperative self-assembly in water. Two weakly interacting low-molecular-weight monomers (cyanuric acid and a modified triaminopyrimidine) are shown to form extremely long supramolecular polymer assemblies that retain water solubility. The complete absence of intermediate assemblies means that the observed equilibrium is between free monomers and supramolecular assemblies. These observations are in excellent agreement with literature values for the free energy of nucleic acid base interactions as well as the calculated free energy penalty for the exposure of hydrophobic structures in water. The results of our study have implications for the design of new self-assembling structures and hydrogel-forming molecules and may provide insights into the origin of the first RNA-like polymers.

  DOI：

  10.1021/ja312155v

文献信息

• Efficient Self-Assembly in Water of Long Noncovalent Polymers by Nucleobase Analogues
  作者：Brian J. Cafferty、Isaac Gállego、Michael C. Chen、Katherine I. Farley、Ramon Eritja、Nicholas V. Hud

  DOI：10.1021/ja312155v

  日期：2013.2.20

  Molecular self-assembly is widely appreciated to result from a delicate balance between several noncovalent interactions and solvation effects. However, current design approaches for achieving self-assembly in water with small, synthetic molecules do not consider all aspects of the hydrophobic effect, in particular the requirement of surface areas greater than 1 nm(2) for an appreciable free energy of hydration. With the concept of a minimum hydrophobic surface area in mind, we designed a system that achieves highly cooperative self-assembly in water. Two weakly interacting low-molecular-weight monomers (cyanuric acid and a modified triaminopyrimidine) are shown to form extremely long supramolecular polymer assemblies that retain water solubility. The complete absence of intermediate assemblies means that the observed equilibrium is between free monomers and supramolecular assemblies. These observations are in excellent agreement with literature values for the free energy of nucleic acid base interactions as well as the calculated free energy penalty for the exposure of hydrophobic structures in water. The results of our study have implications for the design of new self-assembling structures and hydrogel-forming molecules and may provide insights into the origin of the first RNA-like polymers.