2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-{formyl-[(methoxycarbonylmethyl-carbamoyl)-pyridin-3-yl-methyl]-amino}-tetrahydro-pyran-3-yl ester | 909566-07-0

• 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: 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-{formyl-[(methoxycarbonylmethyl-carbamoyl)-pyridin-3-yl-methyl]-amino}-tetrahydro-pyran-3-yl ester
• CAS: 909566-07-0
• 化学式: C₃₇H₅₅N₃O₁₃
• 分子量: 749.856
• InChiKey: OSILRTUBYYGQLT-GHSQPYRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  53.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  203.03
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-{formyl-[(methoxycarbonylmethyl-carbamoyl)-pyridin-3-yl-methyl]-amino}-tetrahydro-pyran-3-yl ester 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 3-(1-ammonio-2-(2-methoxy-2-oxoethylamino)-2-oxoethyl)pyridinium chloride
  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
• 作为产物：
  描述：

  3-吡啶甲醛 、 甲酸 、 异腈基乙酸甲酯 、 2,3,4,6-四-O-叔戊酰基-beta-D-吡喃半乳糖胺 在 zinc(II) chloride 作用下， 以 乙醚 为溶剂， 反应 12.5h， 以88%的产率得到2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-{formyl-[(methoxycarbonylmethyl-carbamoyl)-pyridin-3-yl-methyl]-amino}-tetrahydro-pyran-3-yl ester
  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