adenosine 3'-monophosphate | 135245-29-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核糖核苷3'-磷酸盐
• 英文名称: adenosine 3'-monophosphate
• 英文别名: 3'-monophosphate of adenosine；adenosine 3'-phosphate；3'-AMP；3'-O-phosphonatoadenosine；[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] phosphate
• CAS: 135245-29-3
• 化学式: C₁₀H₁₂N₅O₇P
• 分子量: 345.208
• InChiKey: LNQVTSROQXJCDD-KQYNXXCUSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  192
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  adenosine 3'-monophosphate 、 水 生成 腺苷 、 H3PO4
  参考文献：
  名称：

  Biochemical characterization of the class B acid phosphatase (AphA) of Escherichia coli MG1655

  摘要：

  The AphA enzyme of Escherichia coli, a molecular class B periplasmic phosphatase that belongs to the DDDD superfamily of phosphohydrolases, was purified and subjected to biochemical characterization. Kinetic analysis with several substrates revealed that the enzyme essentially behaves as a broad-spectrum nucleotidase highly active on 3'- and 5'-mononucleotides and monodeoxynucleotides, but not active on cyclic nucleotides, or nucleotides di- and triphosphate. Mononucleotides are degraded to nucleosides, and AphA apparently does not exhibit any nucleotide phosphomutase activity. However, it can transphosphorylate nucleosides in the presence of phosphate donors. Kinetic properties of AphA are consistent with structural data, and suggest a role for the hydrophobic pocket present in the active site crevice, made by residues Phe 56, Leu71, Trp77 and Tyr193, in conferring preferential substrate specificity by accommodating compounds with aromatic rings. AphA was inhibited by several chelating agents, including EDTA, EGTA, 1,10-phenanthroline and dipicolinic acid, with EDTA being apparently the most powerful inhibitor. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.bbapap.2005.08.028
• 作为产物：
  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

文献信息

• Regioselective cleavage of di- and poly-ribonucleotides induced by cyclodextrins (cyclomalto-oligosaccharides)
  作者：Makoto Komiyama

  DOI：10.1016/0008-6215(89)85169-9

  日期：1989.10

  Abstract Cyclodextrins (cyclomalto-oligosaccharides, CDs) induce regioselective cleavage of the 3′,5′-phosphodiester linkages in di- and poly-ribonucleotides at pH 11.08 and 50°. 0.15 m Cyclomaltohexaose (α-CD) mediates the cleavage of CpA, CpC, CpG, and CpU to give 96–97% of cytidine 3′-phosphate together with adenosine, cytidine, guanosine, and uridine, respectively. In the absence of α-CD, 50–52%

  摘要环糊精（环麦芽寡糖，CD）在pH 11.08和50°下诱导二和多核糖核苷酸中3'，5'-磷酸二酯键的区域选择性切割。0.15 m的环己二糖（α-CD）介导CpA，CpC，CpG和CpU的裂解，分别产生96–97％的胞苷3'-磷酸以及腺苷，胞苷，鸟苷和尿苷。在没有α-CD的情况下，形成了50-52％的胞苷2'-磷酸副产物。α-CD还促进了ApA和ApC的腺苷3'-磷酸的形成，GpG的鸟苷3'-磷酸的形成和UpU的尿苷3'-磷酸的形成。相反，β-CD和γ-CD增强了相应的2'-磷酸盐的形成。还实现了poly [A]，poly [C]，poly [G]和poly [U]的区域选择性切割。
• Hydrolysis of Diribonucleoside Monophosphate Diesters Assisted by a Manganese(II) Complex
  作者：Morio Yashiro、Maiko Higuchi、Makoto Komiyama、Youichi Ishii

  DOI：10.1246/bcsj.76.1813

  日期：2003.9

  An Mn2+ complex with 2,2′:6′,2″-terpyridine (terpy) was found to promote the hydrolysis of NpN (NpN = diribonucleoside monophosphate diester) efficiently at pH 7.0 and 50 °C under ambient conditions. The structure of the Mn2+ complex involving a phosphodiester molecule, [(terpy)(dpp)MnII(μ-dpp)2MnII(dpp)(terpy)], dpp = diphenyl phosphate anion, was established by X-ray crystallography, and the coordination mode of Mn2+ to a phosphodiester molecule was considered.

  在常温常压下，于pH 7.0和50°C条件下，发现一种含2,2′:6′,2″-三联吡啶（terpy）的Mn2+配合物能高效促进NpN（NpN = 二核苷酸单磷酸二酯）的水解。通过X射线结晶学确定了涉及磷酸二酯分子的Mn2+配合物[（terpy）（dpp）MnII（μ-dpp）2MnII（dpp）（terpy）]的结构，其中dpp = 二苯基磷酸盐阴离子，并考虑了Mn2+与磷酸二酯分子的配位方式。
• 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
• .alpha.-Cyclodextrin-catalyzed regioselective phosphorus-oxygen(2') cleavages of 2',3'-cyclic monophosphates of ribonucleosides
  作者：Makoto Komiyama

  DOI：10.1021/ja00190a045

  日期：1989.4