(15N5)-4,5,6-triamino-2-hexylthiopyrimidine | 362632-58-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (15N5)-4,5,6-triamino-2-hexylthiopyrimidine
• 英文别名: 2-hexylsulfanyl(1,3-15N2)pyrimidine-4,5,6-tri(15N3)amine
• CAS: 362632-58-4
• 化学式: C₁₀H₁₉N₅S
• 分子量: 246.327
• InChiKey: QGSZHIIADXTWIN-QWWPPVEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (15N5)-4,5,6-triamino-2-hexylthiopyrimidine 、 原甲酸三甲酯 在 盐酸 作用下， 反应 0.25h， 以85%的产率得到(15N5)-2-hexylthioadenine
  参考文献：
  名称：

  (¹⁵N₅)-Labeled Adenine Derivatives:  Synthesis and Studies of Tautomerism by ¹⁵N NMR Spectroscopy and Theoretical Calculations

  摘要：

  Since the nitrogens of nucleosides and nucleotides play an important role in the molecular recognition of these compounds, N-15 NMR became a method of choice in this field. Fully N-15-labeled adenine, required in the latter studies, was obtained in four synthetic steps, in a good yield. Likewise, (N-15(5))-2-hexylthioether-adenine and (N-15(5))-8-Br-adenine were obtained in five synthetic steps from the relatively inexpensive N-15 sources: N-15-NH4Cl, N-15-NH4OH, N-15-NaNO2. Full N-15 labeling of these adenine prototypes enabled to obtain high-resolution 15N NMR spectra of these bases at 60.8 MHz. Furthermore, the spectra suggested the existence of the N3-H species in the tautomeric mixtures of these compounds in solution, in addition to the well-reported N9-H (major) and N7-H (minor) tautomers. These observations were also supported by quantum mechanical calculations of the tautomeric equilibria in the gas phase and in solution of the above-mentioned adenine compounds. The gas-phase tautomeric equilibria were estimated using density functional theory and second-order perturbation theory methods. Solvent effects were included by means of both continuum and discrete solvation models. The observation of the existence of the N3-H tautomer has a clear impact on the possible H-bonding patterns of these adenine prototypes and on their molecular recognition by various biological macromolecules. The above(15)N-labeled analogues are expected to find use as N-15 NMR probes for numerous biochemical studies.

  DOI：

  10.1021/jo010344n
• 作为产物：
  描述：

  (15N5)-4,6-diamino-5-nitroso-2-hexylthiopyrimidine 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 以100%的产率得到(15N5)-4,5,6-triamino-2-hexylthiopyrimidine
  参考文献：
  名称：

  (¹⁵N₅)-Labeled Adenine Derivatives:  Synthesis and Studies of Tautomerism by ¹⁵N NMR Spectroscopy and Theoretical Calculations

  摘要：

  Since the nitrogens of nucleosides and nucleotides play an important role in the molecular recognition of these compounds, N-15 NMR became a method of choice in this field. Fully N-15-labeled adenine, required in the latter studies, was obtained in four synthetic steps, in a good yield. Likewise, (N-15(5))-2-hexylthioether-adenine and (N-15(5))-8-Br-adenine were obtained in five synthetic steps from the relatively inexpensive N-15 sources: N-15-NH4Cl, N-15-NH4OH, N-15-NaNO2. Full N-15 labeling of these adenine prototypes enabled to obtain high-resolution 15N NMR spectra of these bases at 60.8 MHz. Furthermore, the spectra suggested the existence of the N3-H species in the tautomeric mixtures of these compounds in solution, in addition to the well-reported N9-H (major) and N7-H (minor) tautomers. These observations were also supported by quantum mechanical calculations of the tautomeric equilibria in the gas phase and in solution of the above-mentioned adenine compounds. The gas-phase tautomeric equilibria were estimated using density functional theory and second-order perturbation theory methods. Solvent effects were included by means of both continuum and discrete solvation models. The observation of the existence of the N3-H tautomer has a clear impact on the possible H-bonding patterns of these adenine prototypes and on their molecular recognition by various biological macromolecules. The above(15)N-labeled analogues are expected to find use as N-15 NMR probes for numerous biochemical studies.

  DOI：

  10.1021/jo010344n

文献信息

• (¹⁵N₅)-Labeled Adenine Derivatives:  Synthesis and Studies of Tautomerism by ¹⁵N NMR Spectroscopy and Theoretical Calculations
  作者：Avital Laxer、Dan T. Major、Hugo E. Gottlieb、Bilha Fischer

  DOI：10.1021/jo010344n

  日期：2001.8.1

  Since the nitrogens of nucleosides and nucleotides play an important role in the molecular recognition of these compounds, N-15 NMR became a method of choice in this field. Fully N-15-labeled adenine, required in the latter studies, was obtained in four synthetic steps, in a good yield. Likewise, (N-15(5))-2-hexylthioether-adenine and (N-15(5))-8-Br-adenine were obtained in five synthetic steps from the relatively inexpensive N-15 sources: N-15-NH4Cl, N-15-NH4OH, N-15-NaNO2. Full N-15 labeling of these adenine prototypes enabled to obtain high-resolution 15N NMR spectra of these bases at 60.8 MHz. Furthermore, the spectra suggested the existence of the N3-H species in the tautomeric mixtures of these compounds in solution, in addition to the well-reported N9-H (major) and N7-H (minor) tautomers. These observations were also supported by quantum mechanical calculations of the tautomeric equilibria in the gas phase and in solution of the above-mentioned adenine compounds. The gas-phase tautomeric equilibria were estimated using density functional theory and second-order perturbation theory methods. Solvent effects were included by means of both continuum and discrete solvation models. The observation of the existence of the N3-H tautomer has a clear impact on the possible H-bonding patterns of these adenine prototypes and on their molecular recognition by various biological macromolecules. The above(15)N-labeled analogues are expected to find use as N-15 NMR probes for numerous biochemical studies.