| 1204085-37-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1204085-37-9
• 化学式: C₄₆H₇₇IO₉Si₃
• 分子量: 985.273
• InChiKey: PJMAZISPZCTKMZ-BCUGCKRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.55
• 重原子数：
  59.0
• 可旋转键数：
  29.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  90.91
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 2.5h， 以36 mg的产率得到(5S,6S)-6-[(1E,3R,4R,6R,7Z)-6-(tert-butyldimethylsilyloxy)-4-hydroxy-8-iodo-3-methyl-3-(triethylsilyloxy)-octa-1,7-dien-1-yl]-5-(4-(2-[2-(prop-2-yn-1-yloxy)ethoxy]ethoxy)benzyloxy)-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Antitumor antibiotic fostriecin covalently binds to cysteine-269 residue of protein phosphatase 2A catalytic subunit in mammalian cells

  摘要：

  Fostriecin is a phosphate monoester with excellent antitumor activity against mouse leukemia, and it is a potent inhibitor of protein phosphatase (PP) 2A. This compound has been predicted to covalently bind to the Cys269 residue of the PP2A catalytic subunit (PP2Ac) at the alpha,beta-unsaturated lactone via a conjugate addition reaction. However, this binding has not yet been experimentally proven. To confirm such binding, we synthesized biotin-labeled fostriecin (bio-Fos), which has an inhibitory activity against the proliferation of mouse leukemia cells. We showed that fostriecin directly binds to PP2Ac in HeLa S3 cells by pull-down assays using bio-Fos. Moreover, we directly demonstrated that fostriecin covalently binds to the Cys269 residue of PP2Ac by matrix assisted laser desorption/ionization time-of-flight mass spectrometry analysis. From these results, the inhibitory mechanism of fostriecin on PP2A activity is discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.050
• 作为产物：
  描述：

  (5S,6S,1'E,3'R,4'R,6'R,7'Z)-6-[6'-(tert-butyl(dimethyl)silyloxy)-8'-iodo-3'-methyl-3',4'-bis(triethylsilyloxy)-1',7'-octadienyl]-5-hydroxy-5,6-dihydro-2H-pyran-2-one 、 在 trityl tetrafluoroborate 、 二乙二醇 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Antitumor antibiotic fostriecin covalently binds to cysteine-269 residue of protein phosphatase 2A catalytic subunit in mammalian cells

  摘要：

  Fostriecin is a phosphate monoester with excellent antitumor activity against mouse leukemia, and it is a potent inhibitor of protein phosphatase (PP) 2A. This compound has been predicted to covalently bind to the Cys269 residue of the PP2A catalytic subunit (PP2Ac) at the alpha,beta-unsaturated lactone via a conjugate addition reaction. However, this binding has not yet been experimentally proven. To confirm such binding, we synthesized biotin-labeled fostriecin (bio-Fos), which has an inhibitory activity against the proliferation of mouse leukemia cells. We showed that fostriecin directly binds to PP2Ac in HeLa S3 cells by pull-down assays using bio-Fos. Moreover, we directly demonstrated that fostriecin covalently binds to the Cys269 residue of PP2Ac by matrix assisted laser desorption/ionization time-of-flight mass spectrometry analysis. From these results, the inhibitory mechanism of fostriecin on PP2A activity is discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.050