肌苷-3',5'-环磷酸酯 | 3545-76-4

• 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: 肌苷-3',5'-环磷酸酯
• 英文名称: cIMP
• 英文别名: inosine 3',5'-cyclic monophosphate；Inosin 3':5'-cyclisches Phosphat；9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]purin-6-ol
• CAS: 3545-76-4
• 化学式: C₁₀H₁₁N₄O₇P
• mdl: MFCD00038618
• 分子量: 330.194
• InChiKey: DMJWGQPYNRPLGA-KQYNXXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  145
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  腺苷环磷酸酯 在 phosphate buffer 作用下， 反应 5.0h， 以93%的产率得到肌苷-3',5'-环磷酸酯
  参考文献：
  名称：

  AMP Deaminase as a Novel Practical Catalyst in the Synthesis of 6-Oxopurine Ribosides and their Analogs

  摘要：

  Adenylic acid deaminase from Aspergillus niger (AMP deaminase; AMPDA; EC 3.5.4.6) has been introduced as a novel practical catalyst in the synthesis of 6-oxopurine riboside and their analogs. This enzyme has a very broad substrate specificity and has been used on a preparative scale for deamination of several derivatives of adenosine including phosphorylated, cyclic, carbocyclic as well as acyclic analogs. In addition, AMPDA catalyzes dechlorination and demethoxylation of the purine ribosides. Overall substrate specificity of AMPDA is much broader than that of adenosine deaminase which can also be used for the synthesis of 6-oxopurine ribosides. Although the stereoselectivity of AMPDA is modest, this enzyme has successfully been used in the synthesis of a novel antiviral agent, carbovir phosphonate (14), after the carbocyclic component was resolved via lipase-catalyzed hydrolysis or acylation.

  DOI：

  10.1021/jo00103a010

文献信息

• Synthesis of the 3′,5′-Cyclic Phosphates from Unprotected Nucleosides
  作者：H. -G. Genieser、E. Butt、U. Bottin、W. Dostmann、B. Jastorff

  DOI：10.1055/s-1989-27150

  日期：——

  Unprotected nucleosides were phosphorylated with phosphoryl chloride in trialkyl phosphates and subsequently cyclized with base to give 3′,5′-cyclic nucleotides in good yields.

  未保护的核苷在三烷基磷酸酯中用磷酰氯进行磷酸化，随后用碱进行环化，良好产率地得到3′,5′-环状核苷酸。
• Discovery of a cAMP Deaminase That Quenches Cyclic AMP-Dependent Regulation
  作者：Alissa M. Goble、Youjun Feng、Frank M. Raushel、John E. Cronan

  DOI：10.1021/cb4004628

  日期：2013.12.20

  An enzyme of unknown function within the amidohydrolase superfamily was discovered to catalyze the hydrolysis of the universal second messenger, cyclic-3',5'-adenosine monophosphate (cAMP). The enzyme, which we have named CadD, is encoded by the human pathogenic bacterium Leptospira interrogans. Although CadD is annotated as an adenosine deaminase, the protein specifically deaminates cAMP to cyclic-3',5'-inosine monophosphate (cIMP) with a k(cat)/K-m of 2.7 +/- 0.4 X 10(5) M-1 s(-1) and has no activity on adenosine, adenine, or 5'-adenosine monophosphate (AMP). This is the first identification of a deaminase specific for cAMP. Expression of CadD in Escherichia coli mimics the loss of adenylate cyclase in that it blocks growth on carbon sources that require the cAMP-CRP transcriptional activator complex for expression of the cognate genes. The cIMP reaction product cannot replace cAMP as the ligand for CRP binding to DNA in vitro and cIMP is a very poor competitor of cAMP activation of CRP for DNA binding. Transcriptional analyses indicate that CadD expression represses expression of several cAMP-CRP dependent genes. CadD adds a new activity to the cAMP metabolic network and may be a useful tool in intracellular study of cAMP-dependent processes.
• GENIESER, H. -G.;BUTT, E.;BOTTIN, U.;DOSTMANN, W.;JASTORFF, B., SYNTHESIS,(1989) N, C. 53-54
  作者：GENIESER, H. -G.、BUTT, E.、BOTTIN, U.、DOSTMANN, W.、JASTORFF, B.

  DOI：——

  日期：——
• AMP Deaminase as a Novel Practical Catalyst in the Synthesis of 6-Oxopurine Ribosides and their Analogs
  作者：Alexey L. Margolin、David R. Borcherding、Dominique Wolf-Kugel、Nara Margolin

  DOI：10.1021/jo00103a010

  日期：1994.12

  Adenylic acid deaminase from Aspergillus niger (AMP deaminase; AMPDA; EC 3.5.4.6) has been introduced as a novel practical catalyst in the synthesis of 6-oxopurine riboside and their analogs. This enzyme has a very broad substrate specificity and has been used on a preparative scale for deamination of several derivatives of adenosine including phosphorylated, cyclic, carbocyclic as well as acyclic analogs. In addition, AMPDA catalyzes dechlorination and demethoxylation of the purine ribosides. Overall substrate specificity of AMPDA is much broader than that of adenosine deaminase which can also be used for the synthesis of 6-oxopurine ribosides. Although the stereoselectivity of AMPDA is modest, this enzyme has successfully been used in the synthesis of a novel antiviral agent, carbovir phosphonate (14), after the carbocyclic component was resolved via lipase-catalyzed hydrolysis or acylation.