[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[(2S)-2-(pent-4-enoylamino)-3-(4-phenylphenyl)propanoyl]oxy-2-(phosphonooxymethyl)oxolan-3-yl] (2S)-2-(pent-4-enoylamino)-3-(4-phenylphenyl)propanoate | 1332617-51-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: [(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[(2S)-2-(pent-4-enoylamino)-3-(4-phenylphenyl)propanoyl]oxy-2-(phosphonooxymethyl)oxolan-3-yl] (2S)-2-(pent-4-enoylamino)-3-(4-phenylphenyl)propanoate
• CAS: 1332617-51-2
• 化学式: C₅₀H₅₂N₇O₁₁P
• 分子量: 957.977
• InChiKey: OSPTWAMYYNELHM-YQGBBZMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  69
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  256
• 氢给体数：
  5
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[(2S)-2-(pent-4-enoylamino)-3-(4-phenylphenyl)propanoyl]oxy-2-(phosphonooxymethyl)oxolan-3-yl] (2S)-2-(pent-4-enoylamino)-3-(4-phenylphenyl)propanoate 、 adenosine 5'-monophosphate monosodium salt 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以79%的产率得到[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-[[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxymethyl]-4-[(2S)-2-(pent-4-enoylamino)-3-(4-phenylphenyl)propanoyl]oxyoxolan-3-yl] (2S)-2-(pent-4-enoylamino)-3-(4-phenylphenyl)propanoate
  参考文献：
  名称：

  A New Strategy for the Synthesis of Bisaminoacylated tRNAs

  摘要：

  Tandemly activated tRNAs participate effectively in protein synthesis and exhibit superior chemical and biochemical stability compared to the more commonly used singly aminoacylated tRNAs. While several bisaminoacylated tRNAs have been prepared via the T4 RNA ligase-mediated condensation of bisaminoacylated pdCpAs and abbreviated tRNA transcripts (tRNA-C(OH)), the bisaminoacylated pdCpAs are difficult to prepare when using bulky amino acids. Described herein is a new strategy for preparing bisaminoacylated tRNAs, applicable even for bulky amino acids.

  DOI：

  10.1021/ol201993c
• 作为产物：
  描述：

  N-succinimidyl 4-pentenoic acid ester 在 碳酸氢钠 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 108.0h， 生成 (2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-((phosphonooxy)methyl)tetrahydrofuran-3-yl (S)-3-([1,1'-biphenyl]-4-yl)-2-(pent-4-enamido)propanoate 、 [(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[(2S)-2-(pent-4-enoylamino)-3-(4-phenylphenyl)propanoyl]oxy-2-(phosphonooxymethyl)oxolan-3-yl] (2S)-2-(pent-4-enoylamino)-3-(4-phenylphenyl)propanoate
  参考文献：
  名称：

  A New Strategy for the Synthesis of Bisaminoacylated tRNAs

  摘要：

  Tandemly activated tRNAs participate effectively in protein synthesis and exhibit superior chemical and biochemical stability compared to the more commonly used singly aminoacylated tRNAs. While several bisaminoacylated tRNAs have been prepared via the T4 RNA ligase-mediated condensation of bisaminoacylated pdCpAs and abbreviated tRNA transcripts (tRNA-C(OH)), the bisaminoacylated pdCpAs are difficult to prepare when using bulky amino acids. Described herein is a new strategy for preparing bisaminoacylated tRNAs, applicable even for bulky amino acids.

  DOI：

  10.1021/ol201993c