(Z)-4-(3,5-dimethoxy-4-hydroxybenzylidene)-2-methyl-1-propargyl-imidazoline-5-one | 1396370-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (Z)-4-(3,5-dimethoxy-4-hydroxybenzylidene)-2-methyl-1-propargyl-imidazoline-5-one
• 英文别名: (5Z)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-methyl-3-prop-2-ynylimidazol-4-one
• CAS: 1396370-69-6
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: FIXLYZAVVRPURX-GHXNOFRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2'-deoxycytidine-5'-triphosphate 、 (Z)-4-(3,5-dimethoxy-4-hydroxybenzylidene)-2-methyl-1-propargyl-imidazoline-5-one 在 copper(l) iodide 、 trisodium tris(3-sulfophenyl)phosphine 、 palladium diacetate 、 N,N-二异丙基乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 0.75h， 以21%的产率得到5-{3’’’’-[(Z)-4’’-(3’’’,5’’’-dimethoxy-4’’’-hydroxybenzylidene)-2’’-methylimidazoline-5’’-one-1’’-N-yl]-1’’-propyn-1’’’’-yl}-2’-deoxycytidine-5’-O-triphosphate sodium salt
  参考文献：
  名称：

  GFP-like Fluorophores as DNA Labels for Studying DNA–Protein Interactions

  摘要：

  GFP-like 3,5-difluoro-4-hydroxybenzylideneimidazolinone (FBI) and 3,5-bis(methoxy)-4-hydroxy-benzylideneimidazolinone (MBI) labels were attached to dCTP through a propargyl linker, and the resulting labeled nucleotides (dC(MBI)TP and dC(FBI)TP) were used for a facile enzymatic synthesis of oligonucleotide or DNA probes by polymerase-catalyzed primer extension. The MBI/FBI-labeled DNA probes exerted low fluorescence that was increased 2-3.2 times upon binding of a protein. The concept was demonstrated on sequence-specific binding of p53 to dsDNA and on nonspecific binding of single strand binding protein to an oligonucleotide. The FBI label was also used for a time-resolved experiment monitoring a single-nucleotide incorporation followed by primer extension by Vent(exo-) polymerase.

  DOI：

  10.1021/jo301684b
• 作为产物：
  描述：

  丁香醛 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 (Z)-4-(3,5-dimethoxy-4-hydroxybenzylidene)-2-methyl-1-propargyl-imidazoline-5-one
  参考文献：
  名称：

  GFP-like Fluorophores as DNA Labels for Studying DNA–Protein Interactions

  摘要：

  GFP-like 3,5-difluoro-4-hydroxybenzylideneimidazolinone (FBI) and 3,5-bis(methoxy)-4-hydroxy-benzylideneimidazolinone (MBI) labels were attached to dCTP through a propargyl linker, and the resulting labeled nucleotides (dC(MBI)TP and dC(FBI)TP) were used for a facile enzymatic synthesis of oligonucleotide or DNA probes by polymerase-catalyzed primer extension. The MBI/FBI-labeled DNA probes exerted low fluorescence that was increased 2-3.2 times upon binding of a protein. The concept was demonstrated on sequence-specific binding of p53 to dsDNA and on nonspecific binding of single strand binding protein to an oligonucleotide. The FBI label was also used for a time-resolved experiment monitoring a single-nucleotide incorporation followed by primer extension by Vent(exo-) polymerase.

  DOI：

  10.1021/jo301684b

文献信息

• GFP-like Fluorophores as DNA Labels for Studying DNA–Protein Interactions
  作者：Jan Riedl、Petra Ménová、Radek Pohl、Petr Orság、Miroslav Fojta、Michal Hocek

  DOI：10.1021/jo301684b

  日期：2012.9.21

  GFP-like 3,5-difluoro-4-hydroxybenzylideneimidazolinone (FBI) and 3,5-bis(methoxy)-4-hydroxy-benzylideneimidazolinone (MBI) labels were attached to dCTP through a propargyl linker, and the resulting labeled nucleotides (dC(MBI)TP and dC(FBI)TP) were used for a facile enzymatic synthesis of oligonucleotide or DNA probes by polymerase-catalyzed primer extension. The MBI/FBI-labeled DNA probes exerted low fluorescence that was increased 2-3.2 times upon binding of a protein. The concept was demonstrated on sequence-specific binding of p53 to dsDNA and on nonspecific binding of single strand binding protein to an oligonucleotide. The FBI label was also used for a time-resolved experiment monitoring a single-nucleotide incorporation followed by primer extension by Vent(exo-) polymerase.