O-(adenosine-5'-O-yl) N-(L-prolyl)phosphoramidate

• 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: O-(adenosine-5'-O-yl) N-(L-prolyl)phosphoramidate
• 英文别名: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-[[(2S)-pyrrolidin-1-ium-2-carbonyl]amino]phosphinate
• 化学式: C₁₅H₂₂N₇O₇P
• 分子量: 443.356
• InChiKey: BIVNOVXAWQKFMF-JVEUSOJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  207
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  在 ammonium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以65%的产率得到O-(adenosine-5'-O-yl) N-(L-prolyl)phosphoramidate
  参考文献：
  名称：

  Synthesis of new aminoacyl-adenylate analogs having an N-acyl phosphoramidate linkage

  摘要：

  New aminoacyl-adenylate analogs (aa-AMPNs), in which the oxygen atom of the mixed anhydride bond of aminoacyl-adenylates is replaced by an NH group, were synthesized by the reaction of an adenosine 5'-phosphoramidite derivative with appropriately protected amino acid amides. Among various reagents studied for activation of the 5'-phosphoramidite derivative, 5-(4-nitrophenyl)-1H-tetrazole was found to give N-acyl phosphoramidate derivatives in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00570-x

文献信息

• Synthesis and Properties of Aminoacylamido-AMP:  Chemical Optimization for the Construction of an <i>N</i>-Acyl Phosphoramidate Linkage
  作者：Tomohisa Moriguchi、Terukazu Yanagi、Masao Kunimori、Takeshi Wada、Mitsuo Sekine

  DOI：10.1021/jo0008338

  日期：2000.12.1

  This paper describes the design and synthesis of a new type of aminoacyl-adenylate analogue (aa-AMPN) having an N-acyl phosphoramidate linkage where the oxygen atom of the mixed anhydride bond of aminoacyl-adenylate (aa-AMP) is replaced by an amino group. This new type of aa-AMP analogue is expected to be useful as material for studies on the recognition mechanism of the aminoacylation of tRNA and

  本文介绍了具有N-酰基氨基磷酸酯键的新型氨基酰基-腺苷酸类似物（aa-AMPN）的设计和合成，其中氨基酰基-腺苷酸（aa-AMP）的混合酸酐键的氧原子被氨基。这种新型的aa-AMP类似物有望用作研究tRNA氨基酰化和其他生化反应识别机制的材料。羧酰胺的亚磷酰胺衍生物与核苷衍生物的缩合失败，因为活化的亚磷酰胺衍生物不仅与羟基反应，而且与另一种反应性物质反应。通过5'-O-亚磷酰胺基腺苷衍生物与羧酰胺衍生物的反应研究了另一种方法。选择TBTr和TSE基团分别用于保护氨基酸酰胺的氨基和磷酸基。详细研究表明，使用5-（3,5-二硝基苯基）-1H-四唑作为亚磷酰胺的活化催化剂可在10分钟内迅速缩合，从而得到完全保护的aa-AMPN衍生物。没有发生副反应。通过两步程序对这些产物进行脱保护，得到高产率的aa-AMPN衍生物。还证明由此获得的aa-AMPN在酸性和碱性条件下均是稳定的，例如0.1M HCl（pH
• Synthesis of new aminoacyl-adenylate analogs having an N-acyl phosphoramidate linkage
  作者：Tomohisa Moriguchi、Terukazu Yanagi、Takeshi Wada、Mitsuo Sekine

  DOI：10.1016/s0040-4039(98)00570-x

  日期：1998.5

  New aminoacyl-adenylate analogs (aa-AMPNs), in which the oxygen atom of the mixed anhydride bond of aminoacyl-adenylates is replaced by an NH group, were synthesized by the reaction of an adenosine 5'-phosphoramidite derivative with appropriately protected amino acid amides. Among various reagents studied for activation of the 5'-phosphoramidite derivative, 5-(4-nitrophenyl)-1H-tetrazole was found to give N-acyl phosphoramidate derivatives in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.