(1R,3R,4Z,6Z,8E)-{3,10-dihydroxy-1-[(1R,2E)-1-hydroxy-1-methyl-3-((2R)-6-oxo-tetrahydropyran-2-yl)allyl]deca-4,6,8-trien-1-yl} dihydrogen phosphate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,3R,4Z,6Z,8E)-{3,10-dihydroxy-1-[(1R,2E)-1-hydroxy-1-methyl-3-((2R)-6-oxo-tetrahydropyran-2-yl)allyl]deca-4,6,8-trien-1-yl} dihydrogen phosphate
• 英文别名: [(1E,3R,4R,6R,7Z,9Z,11E)-3,6,13-trihydroxy-3-methyl-1-[(2R)-6-oxooxan-2-yl]trideca-1,7,9,11-tetraen-4-yl] dihydrogen phosphate
• 化学式: C₁₉H₂₉O₉P
• 分子量: 432.408
• InChiKey: YJTDXELQHVGORR-DSWNLJKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  福司曲星 在 Stryker's reagent 、 溶剂黄146 作用下， 反应 20.0h， 生成 (1R,3R,4Z,6Z,8E)-{3,10-dihydroxy-1-[(1R,2E)-1-hydroxy-1-methyl-3-((2R)-6-oxo-tetrahydropyran-2-yl)allyl]deca-4,6,8-trien-1-yl} dihydrogen phosphate
  参考文献：
  名称：

  Fundamental Role of the Fostriecin Unsaturated Lactone and Implications for Selective Protein Phosphatase Inhibition

  摘要：

  Key derivatives and analogues of fostriecin were prepared and examined that revealed a fundamental role for the unsaturated lactone and confirmed the essential nature of the phosphate monoester. Thus, an identical 200-fold reduction in protein phosphatase 2A (PP2A) inhibition is observed with either the saturated lactone (7) or with an analogue that lacks the entire lactone (15). This 200-fold increase in PP2A inhibition attributable to the unsaturated lactone potentially may be due to reversible C269 alkylation within the PP beta12-beta13 active site loop accounting for PP2A/4 potency and selectivity.

  DOI：

  10.1021/ja038672n

文献信息

• Fundamental Role of the Fostriecin Unsaturated Lactone and Implications for Selective Protein Phosphatase Inhibition
  作者：Suzanne B. Buck、Christophe Hardouin、Satoshi Ichikawa、Danielle R. Soenen、C.-M. Gauss、Inkyu Hwang、Mark R. Swingle、Kathy M. Bonness、Richard E. Honkanen、Dale L. Boger

  DOI：10.1021/ja038672n

  日期：2003.12.1

  Key derivatives and analogues of fostriecin were prepared and examined that revealed a fundamental role for the unsaturated lactone and confirmed the essential nature of the phosphate monoester. Thus, an identical 200-fold reduction in protein phosphatase 2A (PP2A) inhibition is observed with either the saturated lactone (7) or with an analogue that lacks the entire lactone (15). This 200-fold increase in PP2A inhibition attributable to the unsaturated lactone potentially may be due to reversible C269 alkylation within the PP beta12-beta13 active site loop accounting for PP2A/4 potency and selectivity.