Adenosine 2',3'-cyclic monophosphonate | 62906-30-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: Adenosine 2',3'-cyclic monophosphonate
• 英文别名: adenosine cyclic 2',3'-phosphate；2',3'-cyclic monophosphate of adenosine；adenosine 2',3'-cyclic monophosphate；AMP cyclique-2',3'；adenosine 2′:3′-cyclic monophosphate；2',3'-cAMP；[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2-oxido-2-oxo-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3,2]dioxaphosphol-6-yl]methanol
• CAS: 62906-30-3
• 化学式: C₁₀H₁₁N₅O₆P
• 分子量: 328.201
• InChiKey: KMYWVDDIPVNLME-KQYNXXCUSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  158
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Adenosine 2',3'-cyclic monophosphonate 在 recombinant YybT protein 、 potassium chloride 、 水 、 三羟甲基氨基甲烷盐酸盐 、 magnesium chloride 作用下， 生成 adenosine 3'-monophosphate
  参考文献：
  名称：

  2′,3′-cAMP hydrolysis by metal-dependent phosphodiesterases containing DHH, EAL, and HD domains is non-specific: Implications for PDE screening

  摘要：

  The recent report of 2',3'-cAMP isolated from rat kidney is the first proof of its biological existence, which revived interest in this mysterious molecule. 2',3'-cAMP serves as an extracellular adenosine source, but how it is degraded remains unclear. Here, we report that 2',3'-cAMP can be hydrolyzed by six phosphodiesterases containing three different families of hydrolytic domains, generating invariably 3'-AMP but not 2'-AMP. The catalytic efficiency (k(cat)/K-m) of each enzyme against 2',3'-cAMP correlates with that against the widely used non-specific substrate bis(p-nitrophenyl)phosphate (bis-pNPP), indicating that 2',3'-cAMP is a previously unknown non-specific substrate for PDEs. Furthermore, we show that the exclusive formation of 3'-AMP is due to the P-O2' bond having lower activation energy and is not the result of steric exclusion at enzyme active site. Our analysis provides mechanistic basis to dissect protein function when 2',3'-cAMP hydrolysis is observed. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bbrc.2010.06.107
• 作为产物：
  描述：

  在 aqueous alkali 作用下， 生成 Adenosine 2',3'-cyclic monophosphonate 、 尿嘧啶核苷
  参考文献：
  名称：

  Interconversion and phosphoester hydrolysis of 2',5'- and 3',5'-dinucleoside monophosphates: kinetics and mechanisms

  摘要：

  First-order rate constants for the interconversion and hydrolytic cleavage of several 2',5'-and 3',5'-dinucleoside monophosphates (UpU, UpA, ApU, ApA) have been determined over an acidity range from H0 = -0.2 to H- = 12.4 at 363.2 K. Both reactions proceed at comparable rates at pH < 2 and are of first order with respect to hydronium ion at pH < pK(a) of the phosphate moiety (0.7) and second-order under less acidic conditions (pH 1-2). With dinucleoside monophosphates derived from adenosine, acid-catalyzed depurination of the starting material competes with the phosphate migration and phosphoester hydrolysis at pH < 3. The migration rates extrapolated to zero buffer concentration become pH-independent at pH > 4. Under these conditions the migration is considerably faster than the phosphoester hydrolysis, which exhibits acid catalysis at pH < 5 and base catalysis under more basic conditions. By contrast, hydrolysis of the 5'-phosphoester bond is the only reaction detected in alkaline solutions (pH > 8). The reaction is first order with respect to hydroxide ion at [OH-] < 0.01 mol dm-3 and approaches zero-order dependence at higher alkalinities, where the unesterified 2'- or 3'-hydroxyl group becomes ionized. The mechanisms of different partial reactions, and the effects of base moiety structure (purine vs pyrimidine) on their rates are discussed. The data are compared to the known reaction kinetics of monoalkyl esters of adenosine 2'- and 3'-monophosphates.

  DOI：

  10.1021/jo00018a037

文献信息

• Diguanidinocalix[4]arenes as effective and selective catalysts of the cleavage of diribonucleoside monophosphates
  作者：Riccardo Salvio、Roberta Cacciapaglia、Luigi Mandolini、Francesco Sansone、Alessandro Casnati

  DOI：10.1039/c4ra05751a

  日期：——

  Upper rim diguanidino-cone-calix[4]arenes catalyze the hydrolytic cleavage of diribonucleoside monophosphates in aqueous DMSO with good substrate selectivity and rate accelerations approaching 10⁵-fold in the most favourable substrate-catalyst combinations.

  上缘二胍基-锥-杯[4]芳烃在水性DMSO中催化二核苷酸单磷酸酯的水解裂解，具有良好的底物选择性和速率加速，最有利的底物-催化剂组合中速率加速可达10^5倍。
• Chiral Nanozymes-Gold Nanoparticle-Based Transphosphorylation Catalysts Capable of Enantiomeric Discrimination
  作者：Jack L.-Y. Chen、Cristian Pezzato、Paolo Scrimin、Leonard J. Prins

  DOI：10.1002/chem.201600853

  日期：2016.5.17

  the spontaneous formation of chiral bimetallic catalytic sites that display different activities (kcat) towards the enantiomers of an RNA model substrate. Substrate selectivity is observed when the nanozyme is applied to the cleavage of the dinucleotides UpU, GpG, ApA, and CpC, and remarkable differences in reactivity are observed for the cleavage of the enantiomerically pure dinucleotide UpU.

  首次证明了合成金属酶对RNA的对映选择性。含有手性Zn II结合头基的硫醇已在金纳米颗粒表面自组装。这导致手性双金属催化位点的自发形成，该手性双金属催化位点对RNA模型底物的对映异构体显示出不同的活性（k cat）。当将纳米酶应用于二核苷酸UpU，GpG，ApA和CpC的裂解时，观察到底物选择性，并且对映体纯的二核苷酸UpU的裂解观察到反应性的显着差异。
• Adenosine cyclic 3′,5′-(RP)- and (SP)-phosphoramidates, the first representatives of nucleoside cyclic 3′,5′-phosphoramidates derived from ammonia
  作者：S. Bottka、J. Tomasz

  DOI：10.1016/s0040-4039(00)98869-5

  日期：1985.1

  Adenosine cyclic 3′,5′-phosphoramidate was synthesized by reacting adenosine cyclic 3′,5′-phosphate with POCl3, in trimethyl phosphate for 1 h at O°C, followed by in situ treatment of the reaction mixture with a suspension of (NH4)2CO3 in anhydrous DMF or pyridine or DMF/pyridine mixture for 30 min at 25° C. Diastereoisomers (P)- and (P)- the relative quantities of which depended on the solvent of

  腺苷环3'，5'-磷酸氨基甲酸酯的合成方法是：将腺苷环3'，5'-磷酸与POCl 3在磷酸三甲酯中于0°C反应1小时，然后用悬浮液原位处理反应混合物。 （NH 4）2 CO 3在无水DMF或吡啶或DMF /吡啶混合物中在25°C下放置30分钟。非对映异构体（P）-和（P）-的相对量取决于（NH 4）2的溶剂通过反相分配色谱分离CO 3处理。（R P）-和（S的水解P）-继续进行（在0.1 N HCl中为90％，在0.1 N NaOH中为100％）-POC键断裂。
• Phosphorylation of Nucleosides with Sodium<i>cyclo</i>-Triphosphate
  作者：Mitsutomo Tsuhako、Mayumi Fujimoto、Shigeru Ohashi、Hiroyuki Nariai、Itaru Motooka

  DOI：10.1246/bcsj.57.3274

  日期：1984.11

  3′-deoxyadenosine, 2′-deoxycytidine, and thymidine could not be phosphorylated by P3m. 2) The phosphorylation of adenosine, cytidine, guanosine, and uridine varied strongly, depending on the reaction conditions; mixing ratio, pH, reaction temperature and time. Under conditions of a high mixing ratio of P3m to nucleoside (5:1–10:1), high pH (12–14), high temperature (70–100 °C) for a short time (1–2d)

  在各种条件下（P3m 与核苷的混合比、pH、反应温度和时间）研究了核苷与环三磷酸钠 (P3m) 的磷酸化。1) 腺苷、胞苷、鸟苷和尿苷很容易被 P3m 磷酸化，选择性地形成核苷 2'-单磷酸、3'-单磷酸和 2',3'-环单磷酸。另一方面，2'-脱氧腺苷、3'-脱氧腺苷、2'-脱氧胞苷和胸苷不能被P3m磷酸化。2) 腺苷、胞苷、鸟苷和尿苷的磷酸化程度因反应条件而异；混合比、pH、反应温度和时间。在 P3m 与核苷的高混合比 (5:1–10:1)、高 pH (12–14)、高温（70-100 °C）短时间（1-2d）或低温（室温）长时间（70-150 d），可以在高温下获得核苷2'-和3'-单磷酸。产率（约 50-100%）。3) 在腺苷磷酸化反应的初期...
• Properties of a multifunctional 3′,5′-cyclic nucleotide phosphodiesterase from Lactuca cotyledons: Comparison with mammalian enzymes capable of hydrolysing pyrimidine cyclic nucleotides
  作者：Donato Chiatante、Russell P. Newton、Eric G. Brown

  DOI：10.1016/s0031-9422(00)81799-9

  日期：1987.4

  Abstract Hydrolysis of 3′,5′-cyclic nucleotides by this Lactuca multifunctional cyclic nucleotide phosphodiesterase yields the corresponding 5′-nucleotides. With 2′,3′-cyclic nucleotides, the point of cleavage is affected by the nature of the base. Equimolar amounts of 2′- and 3′-AMP are produced from 2′,3′-cyclic AMP but four times more 3′-CMP than 2′-CMP is produced from 2′,3′-cyclic CMP. With 2′,3′-cyclic

  摘要 通过这种 Lactuca 多功能环核苷酸磷酸二酯酶水解 3',5'-环核苷酸产生相应的 5'-核苷酸。对于 2',3'-环状核苷酸，切割点受碱基性质的影响。等摩尔量的 2'-和 3'-AMP 由 2',3'-环 AMP 产生，但 3'-CMP 是 2'-CMP 的四倍，由 2',3'-环 CMP 产生。与2',3'-环GMP，2'-GMP是唯一的产品。一种环核苷酸的存在会影响另一种环核苷酸的水解速率。对于 3',5'-环核苷酸底物，其他 2',3'- 和 3',5'-环核苷酸表现出混合型抑制。在3',5'-环AMP水解过程中，3',5'-环GMP和2',3'-环AMP的K i 值分别为16和6 μM。再加上 3',5'-环 GMP 的 K m 为 0.73 mM，而 1 的 K m 为 0.73 mM。对于 2',3'-环 AMP 为 12 mM，低 K i 值表明每个核苷酸有一个以上的结合位点可用。对于