(5-aminomethyl-3-hydroxy-2-methylpyridin-4-ylmethyl)carbamic acid tert-butyl ester | 622406-07-9

• 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: (5-aminomethyl-3-hydroxy-2-methylpyridin-4-ylmethyl)carbamic acid tert-butyl ester
• CAS: 622406-07-9
• 化学式: C₁₃H₂₁N₃O₃
• 分子量: 267.328
• InChiKey: SDYVZRIMMZYLSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  97.47
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (5-aminomethyl-3-hydroxy-2-methylpyridin-4-ylmethyl)carbamic acid tert-butyl ester 在 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.0h， 生成 3-[[2-(3-{(2-{2-[bis-(2-methoxycarbonylethyl)amino]ethylcarbamoyl}ethyl)-[4-(tert-butoxycarbonylaminomethyl)-5-methoxymethoxy-6-methylpyridin-3-ylmethyl]amino}propionylamino)ethyl]-(2-methoxycarbonylethyl)amino]propionic acid methyl ester
  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
• 作为产物：
  描述：

  methanesulfonic acid 5-aminomethyl-4-(tert-butoxycarbonylaminomethyl)-2-methylpyridin-3-yl ester 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以100%的产率得到(5-aminomethyl-3-hydroxy-2-methylpyridin-4-ylmethyl)carbamic acid tert-butyl ester
  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