N,N-bisdecyl-3-[(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methylsulfanyl]propionamide | 736157-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N-bisdecyl-3-[(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methylsulfanyl]propionamide
• 英文别名: N,N-bis-decyl-3-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethylsulfanyl)propionamide
• CAS: 736157-62-3
• 化学式: C₃₄H₆₀N₂O₃S
• 分子量: 576.928
• InChiKey: QIIIGZBHLDOKHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.77
• 重原子数：
  40.0
• 可旋转键数：
  23.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  51.66
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N,N-bisdecyl-3-[(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methylsulfanyl]propionamide 在 盐酸 、 manganese(IV) oxide 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 11.0h， 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：

  2,2,8-三甲基-4H-1,3-二恶英并[4,5-c]吡啶-5-甲醇 、 3-[2-bis(decylcarbamoyl)ethyldisulafanyl]-N,N'-bis-decylpropionamide 在 三丁基膦 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以67%的产率得到N,N-bisdecyl-3-[(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methylsulfanyl]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

文献信息

• 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.