3-(4-aminomethyl-5-hydroxy-6-methylpyridin-3-ylmethylsulfanyl)-N,N-bis-decylpropionamide

• 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-methylpyridin-3-ylmethylsulfanyl)-N,N-bis-decylpropionamide
• 英文别名: 3-[[4-(aminomethyl)-5-hydroxy-6-methylpyridin-3-yl]methylsulfanyl]-N,N-didecylpropanamide
• 化学式: C₃₁H₅₇N₃O₂S
• 分子量: 535.878
• InChiKey: CYRUYUKSURMHAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  37
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  丙酮酸 、 3-(4-aminomethyl-5-hydroxy-6-methylpyridin-3-ylmethylsulfanyl)-N,N-bis-decylpropionamide 在 乙二胺四乙酸 作用下， 生成 DL-丙氨酸 、 N,N-bisdecyl-3-(4-formyl-5-hydroxy-6-methylpyridin-3-ylmethylsulfanyl)propionamide
  参考文献：
  名称：

  聚乙烯咪唑作为转氨酶模拟物与疏水结合的吡哆胺衍生物作为辅酶模拟物在水中的高速率和底物选择性

  摘要：

  4-乙烯基咪唑的自由基聚合物和与 1-十二烷基-4-乙烯基咪唑的共聚物用作酶模拟物，在 pH 7.5 和20 摄氏度，使用带有疏水侧链的吡哆胺作为辅酶模拟物。最好的酶模拟物将 indole-3-pyruvic 酸的转氨作用加速了 400 万倍（相对于没有聚合物的速率），比我们之前使用基于聚氮丙啶的酶模拟物实现的速率更高。比较了各种聚乙烯咪唑的性能，包括通过聚合过程的 RAFT 改性制备的那些。

  DOI：

  10.1021/ja9072589
• 作为产物：
  描述：

  2-Methyl-3-hydroxy-4-aminomethyl-5-bromomethylpyridine dihydrobromide 、 3-[2-bis(decylcarbamoyl)ethyldisulafanyl]-N,N'-bis-decylpropionamide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.33h， 生成 3-(4-aminomethyl-5-hydroxy-6-methylpyridin-3-ylmethylsulfanyl)-N,N-bis-decylpropionamide
  参考文献：
  名称：

  Transamination Reactions with Multiple Turnovers Catalyzed by Hydrophobic Pyridoxamine Cofactors in the Presence of Polyethylenimine Polymers

  摘要：

  Pyridoxamines carrying hydrophobic side chains reversibly bind into the hydrophobic core of polyethylenimines and transaminate ketoacids to amino acids with as much as a 725000-fold rate acceleration. Turnover catalysis was achieved by sacrificial oxidative decarboxylation of C-substituted amino acids, which reconverted the pyridoxals to pyridoxamines.

  DOI：

  10.1021/ja048671a

文献信息

• High Rates and Substrate Selectivities in Water by Polyvinylimidazoles as Transaminase Enzyme Mimics with Hydrophobically Bound Pyridoxamine Derivatives as Coenzyme Mimics
  作者：Rachid Skouta、Sujun Wei、Ronald Breslow

  DOI：10.1021/ja9072589

  日期：2009.11.4

  4-vinylimidazole and copolymers with 1-dodecyl-4-vinylimidazole were used as enzyme mimics to transaminate pyruvic acid to alanine, phenylpyruvic acid to phenylalanine, and indole-3-pyruvic acid to tryptophan in water at pH 7.5 and 20 degrees C using pyridoxamines carrying hydrophobic side chains as coenzyme mimics. The best enzyme mimic accelerated the transamination of indole-3-pyruvic acid by a factor of

  4-乙烯基咪唑的自由基聚合物和与 1-十二烷基-4-乙烯基咪唑的共聚物用作酶模拟物，在 pH 7.5 和20 摄氏度，使用带有疏水侧链的吡哆胺作为辅酶模拟物。最好的酶模拟物将 indole-3-pyruvic 酸的转氨作用加速了 400 万倍（相对于没有聚合物的速率），比我们之前使用基于聚氮丙啶的酶模拟物实现的速率更高。比较了各种聚乙烯咪唑的性能，包括通过聚合过程的 RAFT 改性制备的那些。
• Transamination Reactions with Multiple Turnovers Catalyzed by Hydrophobic Pyridoxamine Cofactors in the Presence of Polyethylenimine Polymers
  作者：Lei Liu、Wenjun Zhou、Jason Chruma、Ronald Breslow

  DOI：10.1021/ja048671a

  日期：2004.7.1

  Pyridoxamines carrying hydrophobic side chains reversibly bind into the hydrophobic core of polyethylenimines and transaminate ketoacids to amino acids with as much as a 725000-fold rate acceleration. Turnover catalysis was achieved by sacrificial oxidative decarboxylation of C-substituted amino acids, which reconverted the pyridoxals to pyridoxamines.