(1R-cis)-Bis(1-methylethyl) <2-<4-(2,6-diamino-9H-purin-9-yl)-2-cyclopenten-1-yl>ethyl>-1-phosphonate | 1025832-21-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (1R-cis)-Bis(1-methylethyl) <2-<4-(2,6-diamino-9H-purin-9-yl)-2-cyclopenten-1-yl>ethyl>-1-phosphonate
• 英文别名: 9-[(1R,4R)-4-[2-di(propan-2-yloxy)phosphorylethyl]cyclopent-2-en-1-yl]purine-2,6-diamine
• CAS: 1025832-21-6
• 化学式: C₁₈H₂₉N₆O₃P
• 分子量: 408.44
• InChiKey: FJSRFCFLZKSNLH-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R-cis)-Bis(1-methylethyl) <2-<4-(2,6-diamino-9H-purin-9-yl)-2-cyclopenten-1-yl>ethyl>-1-phosphonate 在 phosphate buffer 作用下， 反应 114.0h， 以92%的产率得到(1R-cis)-Bis(1-methylethyl) <2-<4-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-2-cyclopenten-1-yl>ethyl>-1-phosphonate
  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
• 作为产物：
  描述：

  <2-<4-(Acetyloxy)-2-cyclopenten-1-yl>ethyl>bis(1-methylethyl) ester phosphonic acid 在 四(三苯基膦)钯 、 三苯基膦 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (1R-cis)-Bis(1-methylethyl) <2-<4-(2,6-diamino-9H-purin-9-yl)-2-cyclopenten-1-yl>ethyl>-1-phosphonate
  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

• 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.