methyl 2-(2-(2-(1,3-dioxoisoindolin-2-yl)acetamido)-2-(pyridin-3-yl)acetamido)acetate

• 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: methyl 2-(2-(2-(1,3-dioxoisoindolin-2-yl)acetamido)-2-(pyridin-3-yl)acetamido)acetate
• 英文别名: Methyl 2-[[2-[[2-(1,3-dioxoisoindol-2-yl)acetyl]amino]-2-pyridin-3-ylacetyl]amino]acetate
• 化学式: C₂₀H₁₈N₄O₆
• 分子量: 410.386
• InChiKey: DLVMHHROGGVAHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  Methyl 2-[(2-amino-2-pyridin-3-ylacetyl)amino]acetate 、 邻苯二甲酰甘氨酸 在 N-羟基-7-氮杂苯并三氮唑 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 以80%的产率得到methyl 2-(2-(2-(1,3-dioxoisoindolin-2-yl)acetamido)-2-(pyridin-3-yl)acetamido)acetate
  参考文献：
  名称：

  Investigations of Metal-Coordinated Peptides as Supramolecular Synthons

  摘要：

  This article describes the synthesis and controlled assembly of four model biological-hybrid scaffolds via coordination of a metal complex to four new tripeptides. Each model tripeptide investigated has either a central pyridyl glycyl or a pyridyl alanyl residue between two terminally protected glycines. All tripeptides were coordinated to their complementary recognition unit, a p-methoxy SCS-Pd pincer complex. The assembly events were fully characterized and investigated by H-1 NMR, ES-MS, and isothermal titration calorimetry (ITC) to elucidate how the substitution and spatial distance of the pyridyl moiety to the peptide backbone affects the metal coordination. Using these characterization techniques, we have shown that the metal-coordination events in all cases are fast and quantitative and that the peptide backbones do not interfere with the self-assembly. The ITC analyses showed that the 4-pyridyl tripeptides are the tightest binding ligands toward the palladated pincer complexes with the alanyl derivative being the strongest overall, demonstrating the superiority of the 4-pyridyl peptides over their 3-pyridyl analogues. The measured association constants are comparable to other pincer-pyridine systems in DMSO suggesting that the controlled coordination of the metalated pincer/pyridine interaction is an interesting biological synthon and will allow for the future development of important noncovalent peptide-based hybrid materials.

  DOI：

  10.1021/jo060395q