3-(4-aminomethyl-5-hydroxy-6-methyl-pyridin-3-ylmethylsulfanyl)-N-(2-dimethylamino-ethyl)-propionamide | 477727-77-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(4-aminomethyl-5-hydroxy-6-methyl-pyridin-3-ylmethylsulfanyl)-N-(2-dimethylamino-ethyl)-propionamide
• 英文别名: 3-(4-aminomethyl-5-hydroxy-6-methylpyridin-3-yl-methylsulfanyl)-N-(2-dimethylaminoethyl)propionamide
• CAS: 477727-77-8
• 化学式: C₁₅H₂₆N₄O₂S
• 分子量: 326.463
• InChiKey: YJBCUAIXJSKLHD-UHFFFAOYSA-N

物化性质

• 沸点：
  613.1±55.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.86
• 重原子数：
  22.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  91.48
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-(4-aminomethyl-5-hydroxy-6-methyl-pyridin-3-ylmethylsulfanyl)-N-(2-dimethylamino-ethyl)-propionamide 在 红铝 作用下， 以 四氢呋喃 为溶剂， 生成 4-aminomethyl-5-[3-(2-dimethylamino-ethylamino)-propylsulfanylmethyl]-2-methyl-pyridin-3-ol
  参考文献：
  名称：

  Hydrophobic Effects on Rates and Substrate Selectivities in Polymeric Transaminase Mimics

  摘要：

  The amination of ketoacids to amino acids by pyridoxamine is greatly accelerated when the pyridoxamine is covalently linked to polyethylenimine carrying N-methyl and N-lauryl groups. Michaelis-Menten kinetics is seen with all substrates, from which the effect of the lauryl groups and the methyl groups can be determined with respect to the strength of binding of the substrate and the rate constant k2 within the complex. The polyamine catalyzes the reaction using acid and base groups, the lauryl groups increase k2 by producing a nonpolar medium in which the reaction occurs, and the lauryl groups promote binding of hydrophobic substrates. The result is that the amination of indolepyruvic acid to produce tryptophan is accelerated by 240000-fold.

  DOI：

  10.1021/ja028151k
• 作为产物：
  描述：

  3-[4-(tert-butoxycarbonylaminomethyl)-5-hydroxy-6-methylpyridin-3-ylmethylsulfanyl]propionic acid ethyl ester 在 盐酸 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 3-(4-aminomethyl-5-hydroxy-6-methyl-pyridin-3-ylmethylsulfanyl)-N-(2-dimethylamino-ethyl)-propionamide
  参考文献：
  名称：

  Dendrimeric Pyridoxamine Enzyme Mimics

  摘要：

  PAMAM dendrimers from generations 1-6 were synthesized with pyridoxamine in their core. They transaminated pyruvic and phenylpyruvic acids in water to alanine and phenylalanine, respectively, with Michaelis-Menten kinetics and high effectiveness compared with simple pyridoxamine. The largest dendrimers-similar in size to some globular proteins-were comparable in effectiveness to a previous polyethylenimine (PEI)-pyridoxamine catalyst, and to a protein-pyridoxamine catalyst, but not as effective as a previous PEI-pyridoxamine carrying lauryl hydrophobic groups. The new catalysts showed both general acid/base catalysis by their amino groups and hydrophobic binding of the phenylpyruvate substrate.

  DOI：

  10.1021/ja0374473