Adenosine 5'-triphosphate | 20978-32-9

• 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
• 英文名称: Adenosine 5'-triphosphate
• CAS: 20978-32-9
• 化学式: C₁₀H₁₃N₅O₁₃P₃*3Na
• 分子量: 573.13
• InChiKey: RMJPDRUNCDRUQC-MCDZGGTQSA-K

计算性质

• 辛醇/水分配系数(LogP)：
  -7.04
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  290.45
• 氢给体数：
  3.0
• 氢受体数：
  18.0

反应信息

• 作为产物：
  描述：

  5'-腺嘌呤核苷酸 在 sodium perchlorate 、 三丁基焦磷酸铵 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 25.0h， 生成 Adenosine 5'-triphosphate
  参考文献：
  名称：

  Convenient syntheses of cytidine 5'-triphosphate, guanosine 5'-triphosphate, and uridine 5'-triphosphate and their use in the preparation of UDP-glucose, UDP-glucuronic acid, and GDP-mannose

  摘要：

  DOI：

  10.1021/jo00293a030

文献信息

• Selective Acylation of Nucleosides, Nucleotides, and Glycerol-3-phosphocholine in Water
  作者：Matthew Powner、Christian Fernández-García

  DOI：10.1055/s-0036-1588626

  日期：——

  2′,3′,5′-tri-O-acetyl-nucleosides in water has been developed. Furthermore, a long-chain selective glycerol-3-phosphocholine diacylation is elucidated. These reactions are environmentally benign, rapid, high yielding, and the products are readily purified. Importantly, this reaction may indicate a prebiotically plausible reaction pathway for the selective acylation of key metabolites to facilitate their

  2',3'-二-O-乙酰基-核苷酸-5'-磷酸、2',3'-二-O-乙酰-核苷酸-5'-三磷酸和2',3',5的方便选择性合成'-tri-O-乙酰基-核苷在水中得到了开发。此外，还阐明了长链选择性甘油-3-磷酸胆碱二酰化。这些反应对环境无害、快速、收率高，并且产物易于纯化。重要的是，该反应可能表明关键代谢物的选择性酰化以促进它们并入原代谢中的益生元似是而非的反应途径。
• Efficient Access to Deuterated and Tritiated Nucleobase Pharmaceuticals and Oligonucleotides using Hydrogen‐Isotope Exchange
  作者：Alberto Palazzolo、Sophie Feuillastre、Viktor Pfeifer、Sébastien Garcia‐Argote、Donia Bouzouita、Simon Tricard、Céline Chollet、Elodie Marcon、David‐Alexandre Buisson、Sophie Cholet、François Fenaille、Guy Lippens、Bruno Chaudret、Grégory Pieters

  DOI：10.1002/anie.201813946

  日期：2019.4

  possesses a wide substrate scope and a high solvent tolerability. This novel method facilitates the access to essential diagnostic tools in drug discovery and development: tritiated pharmaceuticals with high specific activities and deuterated oligonucleotides suitable for use as internal standards during LC‐MS quantification.

  描述了一种有效的氢-同位素交换核碱基衍生物的通用方法。在温和的反应条件下，以钌纳米颗粒为催化剂，并以D 2或T 2为同位素源，该反应具有较宽的底物范围和较高的耐溶剂性。这种新颖的方法有助于在药物发现和开发中使用基本的诊断工具：具有高比活性的tri代药物和适合在LC-MS定量过程中用作内部标准品的氘代寡核苷酸。
• Straightforward Ball‐Milling Access to Dinucleoside 5′,5′‐Polyphosphates via Phosphorimidazolide Intermediates
  作者：Lucie Appy、Anaïs Depaix、Xavier Bantreil、Frédéric Lamaty、Suzanne Peyrottes、Béatrice Roy

  DOI：10.1002/chem.201805924

  日期：2019.2.18

  mechanochemical approach to access symmetrical and mixed dinucleoside 5,5′‐polyphosphates is reported. Under ball‐milling conditions, nucleoside 5′‐monophosphates were quantitatively activated using 1,1′‐carbonyldiimidazole, forming their phosphorimidazolide derivatives. The addition of a nucleoside 5′‐mono‐, di‐ or triphosphate directly led to the formation of the corresponding dinucleotides. Benefits

  据报道，采用溶剂辅助的机械化学方法可以得到对称的和混合的5,5'-聚磷酸二核苷。在球磨条件下，使用1,1'-羰基二咪唑定量活化5'-单磷酸核苷，形成其磷酸咪唑啉衍生物。5'-单，二或三磷酸核苷的添加直接导致相应二核苷酸的形成。报告的一锅法的优势包括使用钠或酸形式的未保护核苷酸，被环保的1,1'-羰基二咪唑激活，非干燥条件，反应时间短，转化率高以及易于设置和净化。这项工作为结合核苷酸咪唑化物方法和研磨条件提供了核苷酸缀合物和类似物合成的新视角。
• Ditopic binuclear copper(II) complexes for DNA cleavage
  作者：Israel Carreira-Barral、Miguel Riopedre-Fernández、Andrés de Blas、Jesús Mosquera、M. Eugenio Vázquez、Carlos Platas-Iglesias、David Esteban-Gómez

  DOI：10.1016/j.jinorgbio.2020.110995

  日期：2020.4

  (L2) spacer. The corresponding binuclear CuII and ZnII complexes were prepared and isolated. The X-ray structures of the L1 ligand and the [Cu2L1Cl2]2+ complex evidence an unusual cis/trans conformation of one of the urea groups stabilized by an intramolecular hydrogen bond with the nitrogen atom of the pyridyl spacer. The CuII complexes form rather strong ternary complexes with phosphorylated anions.

  本文中，我们介绍了两个配体的合成，这些配体包含两个通过1,1'-（吡啶-2,6-二基）双（3-乙基脲）（L1）或1,1'-（1,3-亚苯基）双（3-乙基脲）（L2）间隔基。制备并分离了相应的双核CuII和ZnII复合物。L1配体和[Cu2L1CL2] 2+配合物的X射线结构表明，通过一个分子内氢键与吡啶基间隔基的氮原子稳定的脲基之一具有不寻常的顺式/反式构型。CuII配合物与磷酸化的阴离子形成相当强的三元配合物。[Cu2L1] 4+复合物对焦磷酸盐具有相当高的亲和力（在pH 7、25°C时logK11 = 8.19），而[Cu2L2] 4+由于与AMP2-的牢固结合而突出（在pH 7时logK11 = 9.3）。 ，25°C）。使用圆二色性（CD）和发光光谱法监测CuII复合物与小牛胸腺中脱氧核糖核酸（ct-DNA）的相互作用。这些研究表明复合物与ct-DNA有很强的相互作用（对于[Cu2L1]
• Bis- and tris-naphthoimidazolium derivatives for the fluorescent recognition of ATP and GTP in 100% aqueous solution
  作者：Zhaochao Xu、Na Ri Song、Jong Hun Moon、Jin Yong Lee、Juyoung Yoon

  DOI：10.1039/c1ob06344h

  日期：——

  Naphthoimidazolium groups can form unique ionic hydrogen bonds with anions as imidazolium moieties, and in addition, they are fluorescent, so no further elaborative synthesis is needed to introduce a fluorescent group. In this paper, three naphthoimidazolium derivatives were synthesized and studied for the recognition of nucleotides. Compound 1 composed of a single naphthoimidazolium group and quaternary ammonium group did not show any significant fluorescent changes with various anions and nucleotides, such as ATP, GTP, CTP, TTP, UTP, ADP and AMP. A tripodal compound 3 bearing three naphthoimidazolium groups and three quaternary ammonium groups, respectively, showed large fluorescence enhancements with UTP, CTP and TTP and moderate fluorescence enhancements with ATP and pyrophosphate and a fluorescence quenching effect with GTP. On the other hand, compound 2 bearing two naphthoimidazolium groups and two quaternary ammonium groups displayed a selective fluorescence enhancement with ATP and a selective fluorescence quenching effect with GTP in 100% aqueous solution.

  萘咪唑铵基团能够与阴离子形成独特的离子氢键，作为咪唑铵基部分，此外，它们具有荧光特性，因此不需要进一步复杂的合成来引入荧光基团。本文合成了三种萘咪唑铵衍生物，并研究它们对核苷酸的识别。化合物1由单个萘咪唑铵基团和四元铵基团组成，与各种阴离子和核苷酸（如ATP、GTP、CTP、TTP、UTP、ADP及AMP）并未显示出显著的荧光变化。三臂化合物3具有三个萘咪唑铵基团和三个四元铵基团，分别与UTP、CTP和TTP表现出较大的荧光增强，与ATP和焦磷酸盐有适度的荧光增强，而与GTP则显示出荧光猝灭效应。另一方面，化合物2具有两个萘咪唑铵基团和两个四元铵基团，在100%水溶液中对ATP表现出选择性荧光增强，而对GTP则表现出选择性荧光猝灭效应。