N,N-bisdecyl-3-(4-formyl-5-hydroxy-6-methylpyridin-3-ylmethylsulfanyl)propionamide | 736157-54-3

• 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: N,N-bisdecyl-3-(4-formyl-5-hydroxy-6-methylpyridin-3-ylmethylsulfanyl)propionamide
• 英文别名: N,N-didecyl-3-[(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methylsulfanyl]propanamide
• CAS: 736157-54-3
• 化学式: C₃₁H₅₄N₂O₃S
• 分子量: 534.847
• InChiKey: JXJUFEFLNOJLTL-UHFFFAOYSA-N

物化性质

• 沸点：
  671.0±55.0 °C(Predicted)
• 密度：
  1.021±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  37
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  95.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-bisdecyl-3-(4-formyl-5-hydroxy-6-methylpyridin-3-ylmethylsulfanyl)propionamide 在 对甲苯磺酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 8.0h， 生成 5-[2-(bisdecylcarbamoyl)ethylsulfanylmethyl]-4-dimethoxymethyl-3-hydroxy-1,2-dimethylpyridinium iodide
  参考文献：
  名称：

  Hydrophobic and electronic factors in the design of dialkylglycine decarboxylase mimics

  摘要：

  The first functional catalytic mimic of the enzyme dialkylglycine decarboxylase is described. This system utilizes a hydrophobically modified polyethylenimine polymer, a pyridoxamine cofactor, and a 2-aryl-2-alkylglycine sacrificial amine source to convert alpha-keto acids to alpha-amino acids at biologically relevant temperatures with multiple turnovers of the pyridoxamine catalyst. The effects of hydrophobic and electronic factors in the 2,2-disubstituted sacrificial amine source and the pyridoxamine catalyst on turnover frequency and turnover number are explored. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.019
• 作为产物：
  描述：

  N,N-bisdecyl-3-[(5-hydroxy-4-hydroxymethyl-6-methylpyridin-3-yl)methylsulfanyl]propionamide 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以75%的产率得到N,N-bisdecyl-3-(4-formyl-5-hydroxy-6-methylpyridin-3-ylmethylsulfanyl)propionamide
  参考文献：
  名称：

  Hydrophobic and electronic factors in the design of dialkylglycine decarboxylase mimics

  摘要：

  The first functional catalytic mimic of the enzyme dialkylglycine decarboxylase is described. This system utilizes a hydrophobically modified polyethylenimine polymer, a pyridoxamine cofactor, and a 2-aryl-2-alkylglycine sacrificial amine source to convert alpha-keto acids to alpha-amino acids at biologically relevant temperatures with multiple turnovers of the pyridoxamine catalyst. The effects of hydrophobic and electronic factors in the 2,2-disubstituted sacrificial amine source and the pyridoxamine catalyst on turnover frequency and turnover number are explored. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.019
• 作为试剂：
  描述：

  DL-2-氨基-2-苯基丙酸 在 polyethyleneimine polymer 、 N,N-bisdecyl-3-(4-formyl-5-hydroxy-6-methylpyridin-3-ylmethylsulfanyl)propionamide 作用下， 以 various solvent(s) 为溶剂， 生成 苯乙酮
  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.
• Hydrophobic and electronic factors in the design of dialkylglycine decarboxylase mimics
  作者：Jason J. Chruma、Lei Liu、Wenjun Zhou、Ronald Breslow

  DOI：10.1016/j.bmc.2005.05.019

  日期：2005.10

  The first functional catalytic mimic of the enzyme dialkylglycine decarboxylase is described. This system utilizes a hydrophobically modified polyethylenimine polymer, a pyridoxamine cofactor, and a 2-aryl-2-alkylglycine sacrificial amine source to convert alpha-keto acids to alpha-amino acids at biologically relevant temperatures with multiple turnovers of the pyridoxamine catalyst. The effects of hydrophobic and electronic factors in the 2,2-disubstituted sacrificial amine source and the pyridoxamine catalyst on turnover frequency and turnover number are explored. (c) 2005 Elsevier Ltd. All rights reserved.