[Pt(ethylenediamine)(2,2-dimethylmalonic acid(2-))] | 518013-10-0

• 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: [Pt(ethylenediamine)(2,2-dimethylmalonic acid(2-))]
• CAS: 518013-10-0
• 化学式: C₇H₁₄N₂O₄Pt
• 分子量: 385.279
• InChiKey: QKOONQDRNWUMPJ-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  [Pt(ethylenediamine)(2,2-dimethylmalonic acid(2-))] 、 N-acetylated l-methionylglycine 以 重水 为溶剂， 生成 [Pt(ethylenediamine)(2,2-dimethylmalonic acid(2-))(Ac-L-Met-Gly(1-))]
  参考文献：
  名称：

  1H NMR study of the reactions between carboplatin analogues [Pt(en)(Me-mal-O,O′)] and [Pt(en)(Me2-mal-O,O′)] and various methionine- and histidine-containing peptides under physiologically relevant conditions

  摘要：

  H-1 NMR spectroscopy was applied to the study the reactions of [Pt(en)(Me-mal-O,O')] and [Pt(en)(Me-2-mal-O,O')] complexes (en is ethylenediamine, Me-mal and Me-2-mal are bidentate coordinated anions of 2-methylmalonic and 2,2-dimethylmalonic acids, respectively) with N-acetylated Ac-L-Met-Gly and Ac-L-Met-L-His-type peptides (Ac-L-Met-L-His, Ac-L-Met-Gly-L-His-GlyNH(2) and Ac-L-Met-Gly-Gly-L-His-Gly). The use of Me-mal and Me2-mal Pt(II) complexes in the above reactions allows convenient monitoring of their biscarboxylate group via methyl peaks by H-1 NMR measurements. All reactions were realized at 37 degrees C with equimolar amounts of the Pt(II) complex and the dipeptide at pH 7.40 in 50 mM phosphate buffer in D2O. In all these reactions the ring-opened Me-mal and Me-2-mal Pt(II) adducts as an intermediate products were detected in solution for more than 48 h. We found that during this time in the reaction with Ac-L-Met-Gly these monodentate bound malonate ligands have been replaced by water molecule leading to the formation of the corresponding aqua Pt(II)-peptide complex which further promotes the regioselective cleavage of the peptide. However, in the reaction with Ac-L-Met-L-His-type peptides a selective intramolecular replacement of these malonate anions by the N3 imidazole nitrogen atom from histidine residue was occurred. This replacement reaction leads to the formation of the S, N3-macrochelate Pt(II)-peptide complex which was shown as very stable and hydrolytically inactive for more than two weeks. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.11.004
• 作为产物：
  描述：

  Pt(ethylenediamine)(H2O)2(NO3)2 、 二甲基丙二酸 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 3.0h， 以60%的产率得到[Pt(ethylenediamine)(2,2-dimethylmalonic acid(2-))]
  参考文献：
  名称：

  1H NMR study of the reactions between carboplatin analogues [Pt(en)(Me-mal-O,O′)] and [Pt(en)(Me2-mal-O,O′)] and various methionine- and histidine-containing peptides under physiologically relevant conditions

  摘要：

  H-1 NMR spectroscopy was applied to the study the reactions of [Pt(en)(Me-mal-O,O')] and [Pt(en)(Me-2-mal-O,O')] complexes (en is ethylenediamine, Me-mal and Me-2-mal are bidentate coordinated anions of 2-methylmalonic and 2,2-dimethylmalonic acids, respectively) with N-acetylated Ac-L-Met-Gly and Ac-L-Met-L-His-type peptides (Ac-L-Met-L-His, Ac-L-Met-Gly-L-His-GlyNH(2) and Ac-L-Met-Gly-Gly-L-His-Gly). The use of Me-mal and Me2-mal Pt(II) complexes in the above reactions allows convenient monitoring of their biscarboxylate group via methyl peaks by H-1 NMR measurements. All reactions were realized at 37 degrees C with equimolar amounts of the Pt(II) complex and the dipeptide at pH 7.40 in 50 mM phosphate buffer in D2O. In all these reactions the ring-opened Me-mal and Me-2-mal Pt(II) adducts as an intermediate products were detected in solution for more than 48 h. We found that during this time in the reaction with Ac-L-Met-Gly these monodentate bound malonate ligands have been replaced by water molecule leading to the formation of the corresponding aqua Pt(II)-peptide complex which further promotes the regioselective cleavage of the peptide. However, in the reaction with Ac-L-Met-L-His-type peptides a selective intramolecular replacement of these malonate anions by the N3 imidazole nitrogen atom from histidine residue was occurred. This replacement reaction leads to the formation of the S, N3-macrochelate Pt(II)-peptide complex which was shown as very stable and hydrolytically inactive for more than two weeks. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.11.004