[15N5]-2',3',5'-tri-O-benzoyladenosine | 1012308-14-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: [15N5]-2',3',5'-tri-O-benzoyladenosine
• CAS: 1012308-14-3
• 化学式: C₃₁H₂₅N₅O₇
• 分子量: 584.535
• InChiKey: DEVINOMUNOYSFC-KFKBTZBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  157.75
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  [15N5]-2',3',5'-tri-O-benzoyladenosine 在 亚硝酸异戊酯 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以93%的产率得到
  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]-2-hexylthio-2',3',5'-tri-O-benzoyladenosine 在 镍 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以60%的产率得到[15N5]-2',3',5'-tri-O-benzoyladenosine
  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