5'-(4,4'-dimethoxytrityl)-5-methoxyquinazoline-2,4-(1H,3H)-dione ribonucleoside | 1199886-94-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-(4,4'-dimethoxytrityl)-5-methoxyquinazoline-2,4-(1H,3H)-dione ribonucleoside
• CAS: 1199886-94-6
• 化学式: C₃₅H₃₄N₂O₉
• 分子量: 626.663
• InChiKey: WLGQWQQIZKWFMY-CSEBVFCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  46.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  141.47
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5'-(4,4'-dimethoxytrityl)-5-methoxyquinazoline-2,4-(1H,3H)-dione ribonucleoside 、 (异丙氧基硅)氯甲烷 在 二丁基二氯化锡 、 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.42h， 以30%的产率得到2'-(trisisopropylsiloxy)methyl-5'-(4,4'-dimethoxytrityl)-5-methoxyquinazoline-2,4-(1H,3H)-dione ribonucleoside
  参考文献：
  名称：

  FRET Enabled Real Time Detection of RNA-Small Molecule Binding

  摘要：

  A robust analysis and discovery platform for antibiotics targeting the bacterial rRNA A-site has been developed by incorporating a new emissive U surrogate into the RNA and labeling the aminoglycosides with an appropriate fluorescence acceptor. Specifically, a 5-methoxyquinazoline-2,4(1H,3H)-dione-based emissive uracil analogue was identified to be an ideal donor for 7-diethylaminocoumarin-3-carboxylic acid. This donor/acceptor pair displays a critical Forster radius (R-0) of 27 angstrom, a value suitable for an A-site-aminoglycoside assembly. Titrating the coumarin labeled aminoglycosides into the emissive A-site construct, labeled at position U1406, shows a decrease in donor emission (at 395 nm) and concurrent increase of the acceptor emission (at 473 nm). Titration curves, obtained by fitting the donors emission quenching or the augmentation of the acceptors sensitized emission, faithfully generate EC50 values. Titration of unlabeled ligands into the preformed FRET complex showed a continuous increase of the donor emission, with a concurrent decrease of the acceptor emission, yielding valuable data regarding competitive displacement of aminoglycosides by A-site binders. Detection of antibiotic binding is therefore not dependent on changes in the environment of a single fluorophore, but rather on the responsive interaction between two chromophores acting as a FRET pair, facilitating the determination of direct binding and competitive displacement events with FRET accuracy.

  DOI：

  10.1021/ja905767g
• 作为产物：
  描述：

  5-methoxyquinazoline-2,4-(1H,3H)-dione ribonucleoside 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 、 三乙胺 作用下， 反应 8.0h， 以85%的产率得到5'-(4,4'-dimethoxytrityl)-5-methoxyquinazoline-2,4-(1H,3H)-dione ribonucleoside
  参考文献：
  名称：

  FRET Enabled Real Time Detection of RNA-Small Molecule Binding

  摘要：

  A robust analysis and discovery platform for antibiotics targeting the bacterial rRNA A-site has been developed by incorporating a new emissive U surrogate into the RNA and labeling the aminoglycosides with an appropriate fluorescence acceptor. Specifically, a 5-methoxyquinazoline-2,4(1H,3H)-dione-based emissive uracil analogue was identified to be an ideal donor for 7-diethylaminocoumarin-3-carboxylic acid. This donor/acceptor pair displays a critical Forster radius (R-0) of 27 angstrom, a value suitable for an A-site-aminoglycoside assembly. Titrating the coumarin labeled aminoglycosides into the emissive A-site construct, labeled at position U1406, shows a decrease in donor emission (at 395 nm) and concurrent increase of the acceptor emission (at 473 nm). Titration curves, obtained by fitting the donors emission quenching or the augmentation of the acceptors sensitized emission, faithfully generate EC50 values. Titration of unlabeled ligands into the preformed FRET complex showed a continuous increase of the donor emission, with a concurrent decrease of the acceptor emission, yielding valuable data regarding competitive displacement of aminoglycosides by A-site binders. Detection of antibiotic binding is therefore not dependent on changes in the environment of a single fluorophore, but rather on the responsive interaction between two chromophores acting as a FRET pair, facilitating the determination of direct binding and competitive displacement events with FRET accuracy.

  DOI：

  10.1021/ja905767g