[5-(2-aminoethylsulfanylmethyl)-3-hydroxy-2-methylpyridin-4-ylmethyl]carbamic acid tert-butyl ester | 622405-99-6

• 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-(2-aminoethylsulfanylmethyl)-3-hydroxy-2-methylpyridin-4-ylmethyl]carbamic acid tert-butyl ester
• CAS: 622405-99-6
• 化学式: C₁₅H₂₅N₃O₃S
• 分子量: 327.448
• InChiKey: MTQJBYSLRYOETA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  97.47
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [5-(2-aminoethylsulfanylmethyl)-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 5.5h， 生成 3-[{2-[4-(tert-butoxycarbonylaminomethyl)-5-methoxymethoxy-6-methylpyridin-3-ylmethylsulfanyl]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-(2-aminoethylsulfanylmethyl)-4-(tert-butoxycarbonylaminomethyl)-2-methylpyridin-3-yl ester 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以100%的产率得到[5-(2-aminoethylsulfanylmethyl)-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