2-methylmalonic acid(2-) | 13865-62-8

• 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-methylmalonic acid(2-)
• 英文别名: methylmalonate dianion；2-methylmalonate；methylmalonate；2-Methylpropanedioate
• CAS: 13865-62-8
• 化学式: C₄H₄O₄
• 分子量: 116.073
• InChiKey: ZIYVHBGGAOATLY-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methylmalonic acid(2-) 、 辅酶 A 在 malonyl-CoA synthetase MatB from Rhizobium trifolii 、 5’-三磷酸腺苷 作用下， 反应 0.33h， 生成 methylmalonyl-CoA
  参考文献：
  名称：

  突变丙二酸-CoA合成具有改变的聚酮化合物合酶扩展单元生成的特异性。

  摘要：

  定制指南：我们使用结构指导的饱和诱变，然后进行比色筛选，以鉴定具有改变的底物特异性的突变丙二酰-CoA合成酶。一个特定的突变体显示出240倍的特异性变化（见图）。这些突变酶将是有用的工具，用于提供扩展单元以探测聚酮化合物合酶的活性。

  DOI：

  10.1002/cbic.201100383
• 作为产物：
  描述：

  [Pt(ethylenediamine)(2-methylmalonic acid(2-))(Ac-L-Met-Gly-L-His-Gly-NH2(1-))] 以 重水 为溶剂， 生成 [Pt(ethylenediamine)(Ac-L-Met-Gly-L-His-Gly-NH2(1-))] 、 2-methylmalonic 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48 h. We found that during this time in the reaction with Ac-L-Met-Gly these monodentate bound malonate ligands have been replaced by water molecule leading to the formation of the corresponding aqua Pt(II)-peptide complex which further promotes the regioselective cleavage of the peptide.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

文献信息

• Amico, Paola; Bonomo, Raffaele P.; Calì, Rosario, Inorganic Chemistry, 1989, vol. 28, # 18, p. 3555 - 3561
  作者：Amico, Paola、Bonomo, Raffaele P.、Calì, Rosario、Cucinotta, Vincenzo、Daniele, Pier G.、Ostacoli, Giorgio、Rizzarelli, Enrico

  DOI：——

  日期：——
• Kovachy R.J.; Copley S.D.; Allen R.H., J Biol Chem, 1983, 0021-9258, 11415-21
  作者：Kovachy R.J.、Copley S.D.、Allen R.H.

  DOI：——

  日期：——
• 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
  作者：Snežana Rajković、Darko P. Ašanin、Marija D. Živković、Miloš I. Djuran

  DOI：10.1016/j.ica.2012.11.004

  日期：2013.1

  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.
• Mutant Malonyl-CoA Synthetases with Altered Specificity for Polyketide Synthase Extender Unit Generation
  作者：Irina Koryakina、Gavin J. Williams

  DOI：10.1002/cbic.201100383

  日期：2011.10.17

  saturation mutagenesis followed by colorimetric screening to identify mutant malonyl‐CoA synthetases with altered substrate specificity. One particular mutant displayed a 240‐fold shift in specificity (see graphic). These mutant enzymes will be useful tools for providing extender units to probe the activity of polyketide synthases.

  定制指南：我们使用结构指导的饱和诱变，然后进行比色筛选，以鉴定具有改变的底物特异性的突变丙二酰-CoA合成酶。一个特定的突变体显示出240倍的特异性变化（见图）。这些突变酶将是有用的工具，用于提供扩展单元以探测聚酮化合物合酶的活性。