5-azidofluorescein | 1613187-45-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-azidofluorescein
• 英文别名: 5-Azido-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid；5-azido-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• CAS: 1613187-45-3
• 化学式: C₂₀H₁₁N₃O₅
• 分子量: 373.324
• InChiKey: DHECTDATYOZFPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(4-ethynyl)phenyl-6-methyl-1,2,4,5-tetrazine 、 5-azidofluorescein 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以44%的产率得到5-(4-(4-(6-methyl-1,2,4,5-tetrazin-3-yl )phenyl)-1H-1,2,3-triazol-1-yl)fluorescein
  参考文献：
  名称：

  Rigid tetrazine fluorophore conjugates with fluorogenic properties in the inverse electron demand Diels–Alder reaction

  摘要：

  合成了具有结构刚性分子设计的1,2,4,5-四唑荧光团衍生物，采用了Sonogashira和Stille交叉耦合以及铜催化的叠氮-炔烃环加成反应。这些合成的双荧光团系统因受四唑的猝灭而表现出较低的荧光量子产率。观察到的荧光猝灭程度显示出与荧光团和四唑之间的距离有关。通过反向电子需求Diels-Alder环加成反应，荧光的降低被“开启”。时间分辨光谱学表明，BODIPY与四唑之间发生了共振能量转移，这是猝灭机制的基础。合成的共轭物已成功应用于蛋白质标记实验中。

  DOI：

  10.1039/c4ob00245h

文献信息

• Rigid tetrazine fluorophore conjugates with fluorogenic properties in the inverse electron demand Diels–Alder reaction
  作者：Achim Wieczorek、Tiago Buckup、Richard Wombacher

  DOI：10.1039/c4ob00245h

  日期：——

  1,2,4,5-Tetrazine fluorophore derivatives with structurally rigid molecular designs were synthesized using Sonogashira and Stille cross-coupling as well as copper-catalyzed azide–alkyne cycloaddition. The synthesized bichromophoric systems exhibit low fluorescence quantum yields due to quenching by the tetrazine. The extent of fluorescence quenching observed for those systems was shown to depend on the distance between the fluorophore and the tetrazine. The decreased fluorescence is “turned on” by conversion of the tetrazine in the inverse electron demand Diels–Alder cycloaddition. Time resolved spectroscopy indicated resonance energy transfer between BODIPY and the tetrazine as the underlying quenching mechanism. The synthesized conjugates were successfully applied in protein labeling experiments.

  合成了具有结构刚性分子设计的1,2,4,5-四唑荧光团衍生物，采用了Sonogashira和Stille交叉耦合以及铜催化的叠氮-炔烃环加成反应。这些合成的双荧光团系统因受四唑的猝灭而表现出较低的荧光量子产率。观察到的荧光猝灭程度显示出与荧光团和四唑之间的距离有关。通过反向电子需求Diels-Alder环加成反应，荧光的降低被“开启”。时间分辨光谱学表明，BODIPY与四唑之间发生了共振能量转移，这是猝灭机制的基础。合成的共轭物已成功应用于蛋白质标记实验中。