O2,O5-dibenzoyl-1-(6-benzoylamino-purin-9-yl)-3-fluoro-β-D-1,3-dideoxy-xylofuranose | 20535-14-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O2,O5-dibenzoyl-1-(6-benzoylamino-purin-9-yl)-3-fluoro-β-D-1,3-dideoxy-xylofuranose
• 英文别名: O²,O⁵-dibenzoyl-1-(6-benzoylamino-purin-9-yl)-3-fluoro-β-D-1,3-dideoxy-xylofuranose
• CAS: 20535-14-2
• 化学式: C₃₁H₂₄FN₅O₆
• 分子量: 581.56
• InChiKey: XDFLBWKUKGYRPE-WJCHFDDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  134.53
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  O2,O5-dibenzoyl-1-(6-benzoylamino-purin-9-yl)-3-fluoro-β-D-1,3-dideoxy-xylofuranose 在 磷酸三乙酯 、 氨 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 36.0h， 生成 ((2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
  参考文献：
  名称：

  Aplysia californica mediated cyclisation of novel 3′-modified NAD + analogues: a role for hydrogen bonding in the recognition of cyclic adenosine 5′-diphosphate ribose

  摘要：

  Cyclic ADP-ribose mobilizes intracellular Ca2+ in a variety of cells. To elucidate the nature of the interaction between the C3' substituent of cADP-ribose and the cADPR receptor, three analogues of NAD(+) modified in the adenosine ribase (xyloNAD(+) 3'F-xyloNAD(+) and 3'F-NAD(+) were chemically synthesised from D-xylose and adenine starting materials. 3'F-NAD(+) was readily converted to cyclic 3'F-ADP ribose by the action of the cyclase enzyme derived from the mollusc Aplysia californica. XyloNAD(+) and 3'F-xyloNAD(+) were cyclised only reluctantly and in poor yield to afford unstable cyclic products. Biological evaluation of cyclic 3'F-ADP ribose for calcium release in sea urchin egg homogenate gave an EC50 of 1.5 +/- 0.5 muM. This high value suggests that the ability of the C3' substituent to donate a hydrogen bond is crucial for agonism. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.012
• 作为产物：
  描述：

  1,2,5-tri-O-benzoyl-3-deoxy-3-fluoro-D-xylofuranose 、 N6-苯甲酰基腺嘌呤 在 吡啶 、 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 72.0h， 以22%的产率得到O2,O5-dibenzoyl-1-(6-benzoylamino-purin-9-yl)-3-fluoro-β-D-1,3-dideoxy-xylofuranose
  参考文献：
  名称：

  Aplysia californica mediated cyclisation of novel 3′-modified NAD + analogues: a role for hydrogen bonding in the recognition of cyclic adenosine 5′-diphosphate ribose

  摘要：

  Cyclic ADP-ribose mobilizes intracellular Ca2+ in a variety of cells. To elucidate the nature of the interaction between the C3' substituent of cADP-ribose and the cADPR receptor, three analogues of NAD(+) modified in the adenosine ribase (xyloNAD(+) 3'F-xyloNAD(+) and 3'F-NAD(+) were chemically synthesised from D-xylose and adenine starting materials. 3'F-NAD(+) was readily converted to cyclic 3'F-ADP ribose by the action of the cyclase enzyme derived from the mollusc Aplysia californica. XyloNAD(+) and 3'F-xyloNAD(+) were cyclised only reluctantly and in poor yield to afford unstable cyclic products. Biological evaluation of cyclic 3'F-ADP ribose for calcium release in sea urchin egg homogenate gave an EC50 of 1.5 +/- 0.5 muM. This high value suggests that the ability of the C3' substituent to donate a hydrogen bond is crucial for agonism. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.012