2-[[3-hydroxy-2-methyl-5-(phosphonooxymethyl)pyridin-4-yl]methylideneamino]-3-(1H-indol-3-yl)propanoic acid | 35314-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-[[3-hydroxy-2-methyl-5-(phosphonooxymethyl)pyridin-4-yl]methylideneamino]-3-(1H-indol-3-yl)propanoic acid
• CAS: 35314-38-6
• 化学式: C₁₉H₂₀N₃O₇P
• 分子量: 433.357
• InChiKey: MFRRQHVPLFTBMS-UHFFFAOYSA-N

物化性质

• 沸点：
  829.0±75.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  165
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-[[3-hydroxy-2-methyl-5-(phosphonooxymethyl)pyridin-4-yl]methylideneamino]-3-(1H-indol-3-yl)propanoic acid 以 乙醇 、 水 为溶剂， 生成 吡哆胺 5'-磷酸酯 、 sodium β-(3-indolyl)-α-ketopropionate
  参考文献：
  名称：

  Chemical transformations of pyridoxal and pyridoxal 5′-phosphate condensation products with amino acids

  摘要：

  The mechanism ot'cheinical transformations ofpyridoxal and pyridoxal 5'-phosphate condensation products with amino acids is studitd by kinetic measurements. The Schiff bases are shown to be fairly stable in neutral media. In acid media, the Schiff bases are hydrolyzed into the initial components. In alkaline inedia, cleavage of a-hydrogen from tht amino acid fragment and structural rearran-ement into the qUinoid forin followed by hydrolysis of' the]alter with elimination of pyridoxamine and keto acid take place. The rate constants of the chemical transfori nations of the Schiff bases are found to depend on the pH of the medium. It is shown for the first time that the Dhosphate group in the pyridoxal 5'-phosphate fragment catalyzes the a-hydL_ C rooen cleavaoe and strongly accelerates alkaline decomposition of the Schiff bases.

  DOI：

  10.1134/s1070363208060212
• 作为产物：
  描述：

  磷酸吡哆醛 、 DL-色氨酸 以 乙醇 、 水 为溶剂， 生成 2-[[3-hydroxy-2-methyl-5-(phosphonooxymethyl)pyridin-4-yl]methylideneamino]-3-(1H-indol-3-yl)propanoic acid
  参考文献：
  名称：

  Chemical transformations of pyridoxal and pyridoxal 5′-phosphate condensation products with amino acids

  摘要：

  The mechanism ot'cheinical transformations ofpyridoxal and pyridoxal 5'-phosphate condensation products with amino acids is studitd by kinetic measurements. The Schiff bases are shown to be fairly stable in neutral media. In acid media, the Schiff bases are hydrolyzed into the initial components. In alkaline inedia, cleavage of a-hydrogen from tht amino acid fragment and structural rearran-ement into the qUinoid forin followed by hydrolysis of' the]alter with elimination of pyridoxamine and keto acid take place. The rate constants of the chemical transfori nations of the Schiff bases are found to depend on the pH of the medium. It is shown for the first time that the Dhosphate group in the pyridoxal 5'-phosphate fragment catalyzes the a-hydL_ C rooen cleavaoe and strongly accelerates alkaline decomposition of the Schiff bases.

  DOI：

  10.1134/s1070363208060212

文献信息

• Chemical transformations of pyridoxal and pyridoxal 5′-phosphate condensation products with amino acids
  作者：F. V. Pishchugin、I. T. Tuleberdiev

  DOI：10.1134/s1070363208060212

  日期：2008.6

  The mechanism ot'cheinical transformations ofpyridoxal and pyridoxal 5'-phosphate condensation products with amino acids is studitd by kinetic measurements. The Schiff bases are shown to be fairly stable in neutral media. In acid media, the Schiff bases are hydrolyzed into the initial components. In alkaline inedia, cleavage of a-hydrogen from tht amino acid fragment and structural rearran-ement into the qUinoid forin followed by hydrolysis of' the]alter with elimination of pyridoxamine and keto acid take place. The rate constants of the chemical transfori nations of the Schiff bases are found to depend on the pH of the medium. It is shown for the first time that the Dhosphate group in the pyridoxal 5'-phosphate fragment catalyzes the a-hydL_ C rooen cleavaoe and strongly accelerates alkaline decomposition of the Schiff bases.