N²-(p-bromophenyl)-9-β-D-ribofuranosylguanine 5'-phosphate | 131933-89-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: N²-(p-bromophenyl)-9-β-D-ribofuranosylguanine 5'-phosphate
• CAS: 131933-89-6
• 化学式: C₁₆H₁₇BrN₅O₈P*H₃N
• 分子量: 535.248
• InChiKey: XWWUIRDIMBQHAE-DNBRLMRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.52
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  227.05
• 氢给体数：
  7.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N²-(p-bromophenyl)-9-β-D-ribofuranosylguanine 5'-phosphate 在 三丁基焦磷酸铵 、 N,N'-羰基二咪唑 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 8.0h， 以48%的产率得到N2-(p-bromophenyl)-9-β-D-ribofuranosylguanine 5'-triphosphate
  参考文献：
  名称：

  Interaction of GTP derivatives with cellular and oncogenic ras-p21 proteins

  摘要：

  A series of N2-substituted guanosine 5'-triphosphates was synthesized from the corresponding nucleosides. The nucleosides were prepared by treatment of N2-substituted guanines with tetra-O-acetylribose under conditions which maximized the yield of the 9-beta-guanosine isomers. These nucleotides and several sugar- and base-modified analogues of GTP were tested for their ability to bind to cellular and oncogenic forms of the GTP/GDP binding proteins, Ha-ras-p21. Several N2-substituted GTPs showed affinities higher than that of GDP itself, and the N2-[p-(n-butyl)phenyl] derivative bound to the oncogenic mutant, Leu-61 p21, twice as strongly as to the cellular protein. Changes in relative affinities of the nucleotides are discussed with reference to reported crystallographic structures of p21.

  DOI：

  10.1021/jm00108a010
• 作为产物：
  描述：

  4-溴苯胺 在 磷酸三甲酯 、 三氟甲磺酸三甲基硅酯 、 氨 、 三氯氧磷 作用下， 以 甲醇 、 乙二醇甲醚 、 乙腈 为溶剂， 反应 12.0h， 生成 N²-(p-bromophenyl)-9-β-D-ribofuranosylguanine 5'-phosphate
  参考文献：
  名称：

  Interaction of GTP derivatives with cellular and oncogenic ras-p21 proteins

  摘要：

  A series of N2-substituted guanosine 5'-triphosphates was synthesized from the corresponding nucleosides. The nucleosides were prepared by treatment of N2-substituted guanines with tetra-O-acetylribose under conditions which maximized the yield of the 9-beta-guanosine isomers. These nucleotides and several sugar- and base-modified analogues of GTP were tested for their ability to bind to cellular and oncogenic forms of the GTP/GDP binding proteins, Ha-ras-p21. Several N2-substituted GTPs showed affinities higher than that of GDP itself, and the N2-[p-(n-butyl)phenyl] derivative bound to the oncogenic mutant, Leu-61 p21, twice as strongly as to the cellular protein. Changes in relative affinities of the nucleotides are discussed with reference to reported crystallographic structures of p21.

  DOI：

  10.1021/jm00108a010