(15N5)-2-hexylthioadenine | 471920-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (15N5)-2-hexylthioadenine
• 英文别名: [15N5]-2-hexylthioadenine；2-hexylsulfanyl-7H-purin-6-(15N)amine
• CAS: 471920-65-7
• 化学式: C₁₁H₁₇N₅S
• 分子量: 256.322
• InChiKey: QCPMRZQVSLLBPI-CNZCPZEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (15N5)-2-hexylthioadenine 在 镍 作用下， 以25%的产率得到(15N5)-adenine
  参考文献：
  名称：

  Molecular Recognition of Adenosine Deaminase:¹⁵N NMR Studies

  摘要：

  The elucidation of the molecular recognition of adenosine deaminase (ADA), the interpretation, of the catalytic mechanism, and the design of novel inhibitors are based mostly on data obtained for the crystalline state of the enzyme. To obtain evidence for molecular recognition of the physiologically relevant soluble enzyme, rue studied its interactions with the in situ formed inhibitor; 6-OH-purine riboside (HDPR), by 1D-N-15- and 2D-(H-1-N-15)- NMR using the labeled primary inhibitor [N-15(4)]-PR. We synthesized both [N-15(4)]-PR and an [N-15(4)]-HDPR model, from relatively inexpensive N-15 sources. The (N-15(4))-HDPR model was used to simulate H-bonding and possible Zn2+-coordination of HDPR with ADA. We also explored possible ionic interactions between PR and ADA by N-15-NMR monitored pH-titrations of (N-15(4))-PR. Finally, we investigaled the [N-15(4)]-PR-ADA 1:1 complex by 2D-(H-1-N-15) NMR. We found that HDPR recognition determinants in ADA do not include any ionic-interactions. HDPR NI H is an H-bond acceptor, and not an H-bond donor: Despite the proximity of N7 to the Zn2+-ion, no coordination occurs; instead, N7 is an H-bond acceptor. We found an overall agreement between the crystallographic data for the crystallized ADA:HDPR complex anal the N-15-NMR signals for the corresponding soluble complex. This finding justifies the use of ADA's crystallographic data for the design of novel inhibitors.

  DOI：

  10.1080/15257770601112713
• 作为产物：
  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

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.
• Molecular Recognition of Adenosine Deaminase:¹⁵N NMR Studies
  作者：Avital Laxer、Hugo E. Gottlieb、Bilha Fischer

  DOI：10.1080/15257770601112713

  日期：2007.3

  The elucidation of the molecular recognition of adenosine deaminase (ADA), the interpretation, of the catalytic mechanism, and the design of novel inhibitors are based mostly on data obtained for the crystalline state of the enzyme. To obtain evidence for molecular recognition of the physiologically relevant soluble enzyme, rue studied its interactions with the in situ formed inhibitor; 6-OH-purine riboside (HDPR), by 1D-N-15- and 2D-(H-1-N-15)- NMR using the labeled primary inhibitor [N-15(4)]-PR. We synthesized both [N-15(4)]-PR and an [N-15(4)]-HDPR model, from relatively inexpensive N-15 sources. The (N-15(4))-HDPR model was used to simulate H-bonding and possible Zn2+-coordination of HDPR with ADA. We also explored possible ionic interactions between PR and ADA by N-15-NMR monitored pH-titrations of (N-15(4))-PR. Finally, we investigaled the [N-15(4)]-PR-ADA 1:1 complex by 2D-(H-1-N-15) NMR. We found that HDPR recognition determinants in ADA do not include any ionic-interactions. HDPR NI H is an H-bond acceptor, and not an H-bond donor: Despite the proximity of N7 to the Zn2+-ion, no coordination occurs; instead, N7 is an H-bond acceptor. We found an overall agreement between the crystallographic data for the crystallized ADA:HDPR complex anal the N-15-NMR signals for the corresponding soluble complex. This finding justifies the use of ADA's crystallographic data for the design of novel inhibitors.