{5-[2-(2-aminoethylcarbamoyl)ethylsulfanylmethyl]-3-hydroxy-2-methylpyridin-4-ylmethyl}carbamic acid tert-butyl ester | 622405-81-6

• 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-(2-aminoethylcarbamoyl)ethylsulfanylmethyl]-3-hydroxy-2-methylpyridin-4-ylmethyl}carbamic acid tert-butyl ester
• CAS: 622405-81-6
• 化学式: C₁₈H₃₀N₄O₄S
• 分子量: 398.527
• InChiKey: BSDUHJIEDQGWIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  126.57
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  丙烯酸甲酯（MA） 、 {5-[2-(2-aminoethylcarbamoyl)ethylsulfanylmethyl]-3-hydroxy-2-methylpyridin-4-ylmethyl}carbamic acid tert-butyl ester 以 甲醇 为溶剂， 反应 12.0h， 以72%的产率得到3-[(2-{3-[4-(tert-butoxycarbonylaminomethyl)-5-hydroxy-6-methylpyridin-3-ylmethylsulfanyl]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：

  pyridoxamine dihydrochloride 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 15.25h， 生成 {5-[2-(2-aminoethylcarbamoyl)ethylsulfanylmethyl]-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