Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-{4-[2-[4-(7-acetoxy-2-oxo-2H-chromene-3-carbonyl)-piperazin-1-yl]-1-(4-nitro-phenoxycarbonyloxy)-2-oxo-ethyl]-phenoxy}-tetrahydro-pyran-4-yl ester | 919350-85-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-{4-[2-[4-(7-acetoxy-2-oxo-2H-chromene-3-carbonyl)-piperazin-1-yl]-1-(4-nitro-phenoxycarbonyloxy)-2-oxo-ethyl]-phenoxy}-tetrahydro-pyran-4-yl ester
• CAS: 919350-85-9
• 化学式: C₄₅H₄₃N₃O₂₁
• 分子量: 961.844
• InChiKey: VYFIPHRECRQLDK-OGYLQTFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  69.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  299.46
• 氢给体数：
  0.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-{4-[2-[4-(7-acetoxy-2-oxo-2H-chromene-3-carbonyl)-piperazin-1-yl]-1-(4-nitro-phenoxycarbonyloxy)-2-oxo-ethyl]-phenoxy}-tetrahydro-pyran-4-yl ester 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 4-[[4-[[2-[4-(7-hydroxy-2-oxochromene-3-carbonyl)piperazin-1-yl]-2-oxo-1-[4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethoxy]carbonylamino]cyclohexyl]carbamoyl]-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
  参考文献：
  名称：

  Design and Synthesis of an Enzyme Activity-Based Labeling Molecule with Fluorescence Spectral Change

  摘要：

  Methods of covalent labeling of a specific tag protein with small-molecular dyes play an important role in studying dynamic behaviors of proteins in living cells. On the basis of quinone methide chemistry, we designed and synthesized a beta-galactosidase labeling probe, CMFbeta-gal, which shows a fluorescence wavelength change accompanying the labeling reaction, owing to fluorescence resonance energy transfer (FRET). Since the FRET efficiency changes accompanying the labeling reaction, fluorescence of labeled protein can be observed separately from that of the unreacted probe, so immediate detection of the target protein is possible. This is the first report of a protein labeling probe which features a change of fluorescence wavelength upon reaction, allowing the labeled protein to be detected even in the presence of unreacted probe.

  DOI：

  10.1021/ja0657307
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 palladium on activated charcoal 吡啶 、 氢气 、 caesium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-{4-[2-[4-(7-acetoxy-2-oxo-2H-chromene-3-carbonyl)-piperazin-1-yl]-1-(4-nitro-phenoxycarbonyloxy)-2-oxo-ethyl]-phenoxy}-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Design and Synthesis of an Enzyme Activity-Based Labeling Molecule with Fluorescence Spectral Change

  摘要：

  Methods of covalent labeling of a specific tag protein with small-molecular dyes play an important role in studying dynamic behaviors of proteins in living cells. On the basis of quinone methide chemistry, we designed and synthesized a beta-galactosidase labeling probe, CMFbeta-gal, which shows a fluorescence wavelength change accompanying the labeling reaction, owing to fluorescence resonance energy transfer (FRET). Since the FRET efficiency changes accompanying the labeling reaction, fluorescence of labeled protein can be observed separately from that of the unreacted probe, so immediate detection of the target protein is possible. This is the first report of a protein labeling probe which features a change of fluorescence wavelength upon reaction, allowing the labeled protein to be detected even in the presence of unreacted probe.

  DOI：

  10.1021/ja0657307