2-amino-8-pyridin-1-ium-1-yl-7H-purin-6-olate | 432550-45-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 2-amino-8-pyridin-1-ium-1-yl-7H-purin-6-olate
• CAS: 432550-45-3
• 化学式: C₁₀H₈N₆O
• 分子量: 228.213
• InChiKey: VZSPUCNKOJTBQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.87
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102.64
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-amino-8-pyridin-1-ium-1-yl-7H-purin-6-olate 在 盐酸 作用下， 以94%的产率得到1-(2-Amino-6-oxo-6,9-dihydro-1H-purin-8-yl)-pyridinium; chloride
  参考文献：
  名称：

  Synthesis, Tautomerism and Calculations of Mesomeric Betaines of Guanine

  摘要：

  Reaction of purine-N-oxide (4) with 4-(dimethylamino)pyridine and acetyl chloride, followed by the treatment with hydrochloric acid gave the purine-pyridinium salt (6) which was deprotonated to the mesomeric betaine (7). Depending on the reaction conditions, 4-methylpyridine and pyridine, respectively, converted the nucleoside (8) into the pyridinium salts (9) and (10), or into the mesomeric betaines (11) and (12). According to calculations, the conjugated tautomers (A-D) of betaine (7) are more stable than the cross-conjugated tautomer (7E).

  DOI：

  10.3987/com-02-9634
• 作为产物：
  描述：

  1-(guanosin-8-yl)pyridinium bromide 在 Amberlite IRA-93 (OH^--form) 作用下， 以 水 为溶剂， 以100%的产率得到2-amino-8-pyridin-1-ium-1-yl-7H-purin-6-olate
  参考文献：
  名称：

  Synthesis, Tautomerism and Calculations of Mesomeric Betaines of Guanine

  摘要：

  Reaction of purine-N-oxide (4) with 4-(dimethylamino)pyridine and acetyl chloride, followed by the treatment with hydrochloric acid gave the purine-pyridinium salt (6) which was deprotonated to the mesomeric betaine (7). Depending on the reaction conditions, 4-methylpyridine and pyridine, respectively, converted the nucleoside (8) into the pyridinium salts (9) and (10), or into the mesomeric betaines (11) and (12). According to calculations, the conjugated tautomers (A-D) of betaine (7) are more stable than the cross-conjugated tautomer (7E).

  DOI：

  10.3987/com-02-9634

文献信息

• Synthesis and Base-Pairing of Self-Complementary Mesomeric Betaines of Guanine
  作者：Andreas Schmidt、Nikoloz Kobakhidze

  DOI：10.1246/cl.2002.222

  日期：2002.2

  Substitution of 8-H of guanine-N-oxide was accomplished by pyridine, 4-dimethylaminopyridine and acetyl chloride, respectively, to give a cationic purine base after hydrolysis. Deprotonation formed mesomeric betaines of guanine. ESI mass spectrometry and 1H NMR revealed their self-complementarity. Base-pairing to cytosine was observed with a fully protected DNA model compound.

  分别用吡啶、4-二甲氨基吡啶和乙酰氯取代鸟嘌呤-N-氧化物的8-H，水解后得到阳离子嘌呤碱。去质子化形成鸟嘌呤的中间体甜菜碱。ESI 质谱和 1 H NMR 揭示了它们的自互补性。使用完全保护的 DNA 模型化合物观察到与胞嘧啶的碱基配对。