腺苷-5'-三偏磷酸酯 | 53355-60-5

• 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
• 中文名称: 腺苷-5'-三偏磷酸酯
• 中文别名: 5'-O-(4,6-二羟基-2,4,6-三羟基-1,3,5,2,4,6-三噁三磷杂己环-2-基)腺苷
• 英文名称: adenosine 5'-trimetaphosphate
• 英文别名: Adenosine-5'-trimetaphosphate；(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-[(4,6-dihydroxy-2,4,6-trioxo-1,3,5,2λ5,4λ5,6λ5-trioxatriphosphinan-2-yl)oxymethyl]oxolane-3,4-diol
• CAS: 53355-60-5
• 化学式: C₁₀H₁₄N₅O₁₂P₃
• 分子量: 489.169
• InChiKey: AJXBDVJYPUYBBS-KQYNXXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  248
• 氢给体数：
  5
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  腺苷-5'-三偏磷酸酯 生成 adenosine 5'-triphosphate 、 ADP
  参考文献：
  名称：

  A novel synthesis of nucleoside 5′-triphosphates

  摘要：

  已经实现了核糖核苷酸5'-三磷酸的便捷合成，通过将未保护的核苷与磷酰氯进行一锅反应，然后在使用二甲基甲酰胺存在的条件下，用三正丁基铵磷酸盐处理生成的磷酸二氯酯，可以良好收率（>60%）获得目标产物。

  DOI：

  10.1039/c39910001276
• 作为产物：
  描述：

  2C₈H₂₀N⁽¹⁺⁾*C₁₀H₁₄N₅O₁₃P₃^(2-) 在 N,N'-二环己基碳二亚胺 作用下， 反应 3.0h， 生成 腺苷-5'-三偏磷酸酯
  参考文献：
  名称：

  激酶催化磷酸化中的可点击 5'-γ-二茂铁基三磷酸腺苷生物偶联物

  摘要：

  可点击的共底物：合成了一种含有可点击位点的三功能 5'-γ-二茂铁三磷酸腺苷 (Fc-ATP) 衍生物（见图）。该化合物是激酶催化磷酸化反应中的有效辅助底物，可通过电化学和免疫分析检测方法进行检测。可点击的反应位点使直接修改成为可能，极大地扩展了它的应用范围。

  DOI：

  10.1002/chem.201405510

文献信息

• NUCLEOTIDE TRIPHOSPHATE WITH AN ELECTROACTIVE LABEL CONJUGATED TO THE GAMMA PHOSPHATE
  申请人：Kraatz Heinz-Bernhard

  公开号：US20110218114A1

  公开（公告）日：2011-09-08

  A nucleotide triphosphate (NTP) participates in a phosphorylation reaction, wherein a phosphate group is transferred from the NTP to a substrate by a kinase. Provision in a kinase reaction of a NTP whose gamma phosphate is conjugated to an electroactive label results in the transfer of the gamma phosphate-electroactive label conjugate from the NTP to the substrate. The electroactive label is an organic moiety such as a quinone or a nitroheterocycle, or is a metallocene such as a ferrocene or a cobaltocene. Upon transfer of the gamma phosphate-electroactive label conjugate to an electrode-bound substrate by a kinase, the phosphorylation event is detected electrochemically by cyclic voltammetry. Phosphorylation can also be detected by mass spectrometry of a substrate carrying the electroactive label-conjugated gamma phosphate. NTP comprising the gamma phosphate-electroactive label conjugate is used in methods of detecting the presence of a kinase in a sample, screening candidate compounds that modulate kinase activity, and in methods of diagnosing a disease associated with a kinase.

  核苷酸三磷酸（NTP）参与磷酸化反应，其中通过激酶，将磷酸基从NTP转移至底物。在激酶反应中，提供一个将伽马磷酸酯化为电活性标记的NTP，结果将伽马磷酸酯-电活性标记共轭物从NTP转移至底物。电活性标记是一种有机基团，例如醌或硝基杂环，或是一种金属茂基，例如二茂铁或二茂钴。当伽马磷酸酯-电活性标记共轭物通过激酶转移至电极结合的底物时，通过循环伏安法可以电化学地检测到磷酸化事件。磷酸化还可以通过携带电活性标记共轭伽马磷酸酯的底物的质谱分析来检测。含有伽马磷酸酯-电活性标记共轭物的NTP用于检测样品中激酶的存在，筛选调节激酶活性的候选化合物，并用于诊断与激酶相关的疾病的方法。
• Species- or isozyme-specific enzyme inhibitors. 4. Design of a two-site inhibitor of adenylate kinase with isozyme selectivity
  作者：Alexander Hampton、Francis Kappler、Donald Picker

  DOI：10.1021/jm00348a006

  日期：1982.6
• US5536822A
  申请人：——

  公开号：US5536822A

  公开（公告）日：1996-07-16
• [EN] NUCLEOTIDE TRIPHOSPHATE WITH AN ELECTROACTIVE LABEL CONJUGATED TO THE GAMMA PHOSPHATE<br/>[FR] NOUVEAU NUCLÉOTIDE TRIPHOSPHATE ÉLECTROACTIF
  申请人：KRAATZ BERNIE

  公开号：WO2009039639A1

  公开（公告）日：2009-04-02

  A nucleotide triphosphate (NTP) participates in a phosphorylation reaction, wherein a phosphate group is transferred from the NTP to a substrate by a kinase. Provision in a kinase reaction of a NTP whose gamma phosphate is conjugated to an electroactive label results in the transfer of the gamma phosphate-electroactive label conjugate from the NTP to the substrate. The electroactive label is an organic moiety such as a quinone or a nitrohetercycle, or is a metallocene such as a ferrocene or a cobaltocene. Upon transfer of the gamma phosphate-electroactive label conjugate to an electrode-bound substrate by a kinase, the phosphorylation event is detected electrochemically by cyclic voltammetry. Phosphorylation can also be detected by mass spectrometry of a substrate carrying the electroactive label-conjugated gamma phosphate. NTP comprising the gamma phosphate-electroactive label conjugate is used in methods of detecting the presence of a kinase in a sample, screening candidate compounds that modulate kinase activity, and in methods of diagnosing a disease associated with a kinase.