pp5'(br⁸A)2'p5'(br⁸A)2'p5'(br⁸A) | 84824-01-1

• 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: pp5'(br⁸A)2'p5'(br⁸A)2'p5'(br⁸A)
• 英文别名: pp5''(br8A)2''p5''(br8A)2''p5''(br8A)；[(2R,3R,4R,5R)-5-(6-amino-8-bromopurin-9-yl)-4-[[(2R,3R,4R,5R)-5-(6-amino-8-bromopurin-9-yl)-4-[[(2R,3S,4R,5R)-5-(6-amino-8-bromopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-3-hydroxyoxolan-2-yl]methyl phosphono hydrogen phosphate
• CAS: 84824-01-1
• 化学式: C₃₀H₃₆Br₃N₁₅O₂₂P₄
• 分子量: 1322.31
• InChiKey: ZKVPZHIVJJYSGT-FJVAVWNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.7
• 重原子数：
  74
• 可旋转键数：
  18
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  542
• 氢给体数：
  12
• 氢受体数：
  34

反应信息

• 作为产物：
  描述：

  p5'(br⁸A)2'p5'(br⁸A)2'p5'(br⁸A) 在 咪唑 、 tris(tributylammonium) phosphate 、 2,2'-二硫二吡啶 、 triethylammonium salt 、 三乙胺 、 三苯基膦 作用下， 生成 pp5'(br⁸A)2'p5'(br⁸A)2'p5'(br⁸A)
  参考文献：
  名称：

  Synthesis and biological activities of oligo(8-bromoadenylates) as analogs of 5'-O-triphosphoadenylyl(2'.fwdarw.5')adenylyl(2'.fwdarw.5')adenosine

  摘要：

  The 8-bromoadenosine analogue of 5'-O-triphosphoadenylyl(2'----5')adenylyl(2'----5')adenosine (2-5A) and its derivatives were synthesized, and their biological activity was evaluated in mouse L cell extracts. All compounds, except 5'-dephosphorylated "cores" bound to the 2-5A-dependent endonuclease with a relative activity, depending on the derivative, of 1 to 0.035 of that of 2-5A trimer. 8-Bromoadenylate trimer 5'-mono-, -di, and -triphosphates inhibited protein synthesis with a relative activity of 0.0023, 0.050, and 0.015 compared to 2-5A. Tetramer 5'-monophosphate also inhibited protein synthesis (relative activity 0.0033). The corresponding pentamer 5'-monophosphate did not; however, the pentamer 5'-diphosphate was able to inhibit translation (relative activity 0.0092). All compounds that possessed inhibitory activity in the protein synthesis inhibition assay gave ribosomal RNA cleavage patterns characteristic of the action of 2-5A-dependent endonuclease. Thus, 8-bromination of the all of the adenine rings of 2-5A leads to 20- to 70-fold reduction in the biological activity of the corresponding 5'-di- and -triphosphate, respectively; however, this same alteration of the three adenine moieties gives rise to a 5'-monophosphate with much enhanced translational inhibitory activity compared to the parent 2-5A trimer 5'-monophosphate.

  DOI：

  10.1021/jm00156a020

文献信息

• Synthesis and biological activities of oligo(8-bromoadenylates) as analogs of 5'-O-triphosphoadenylyl(2'.fwdarw.5')adenylyl(2'.fwdarw.5')adenosine
  作者：Krystyna Lesiak、Paul F. Torrance

  DOI：10.1021/jm00156a020

  日期：1986.6

  The 8-bromoadenosine analogue of 5'-O-triphosphoadenylyl(2'----5')adenylyl(2'----5')adenosine (2-5A) and its derivatives were synthesized, and their biological activity was evaluated in mouse L cell extracts. All compounds, except 5'-dephosphorylated "cores" bound to the 2-5A-dependent endonuclease with a relative activity, depending on the derivative, of 1 to 0.035 of that of 2-5A trimer. 8-Bromoadenylate trimer 5'-mono-, -di, and -triphosphates inhibited protein synthesis with a relative activity of 0.0023, 0.050, and 0.015 compared to 2-5A. Tetramer 5'-monophosphate also inhibited protein synthesis (relative activity 0.0033). The corresponding pentamer 5'-monophosphate did not; however, the pentamer 5'-diphosphate was able to inhibit translation (relative activity 0.0092). All compounds that possessed inhibitory activity in the protein synthesis inhibition assay gave ribosomal RNA cleavage patterns characteristic of the action of 2-5A-dependent endonuclease. Thus, 8-bromination of the all of the adenine rings of 2-5A leads to 20- to 70-fold reduction in the biological activity of the corresponding 5'-di- and -triphosphate, respectively; however, this same alteration of the three adenine moieties gives rise to a 5'-monophosphate with much enhanced translational inhibitory activity compared to the parent 2-5A trimer 5'-monophosphate.