P-dThd-P-dGuo-P-dThd-P-dThd

• 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: P-dThd-P-dGuo-P-dThd-P-dThd
• 英文别名: [(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-[hydroxy-[[(2R,3S,5R)-3-[hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]oxyoxolan-2-yl]methyl [(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-(phosphonooxymethyl)oxolan-3-yl] hydrogen phosphate
• 化学式: C₅₂H₆₅N₁₂O₂₉P₄Pol
• 分子量: 1259.8
• InChiKey: ZCFBCIXSQDRPCR-WUHZVHKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.2
• 重原子数：
  83
• 可旋转键数：
  22
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  525
• 氢给体数：
  11
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  P-dThd-P-dGuo-P-dThd-P-dThd 、 二甲基亚砜 在 二氯乙酸 、 N,N'-二异丙基碳二亚胺 、 ammonium hydroxide 、 水 作用下， 以 乙腈 为溶剂， 反应 16.17h， 以90%的产率得到5'-O-Phosphoryl-thymidylyl-(3'-5')-thymidylyl-(3'-5')-thymidin
  参考文献：
  名称：

  Phosphorylating Reagent-Free Synthesis of 5′-Phosphate Oligonucleotides by Controlled Oxidative Degradation of Their 5′-End

  摘要：

  The 5'-phosphorylated oligonucleotides (5'-pONs) are currently synthesized using expensive and sensitive modified phosphoramidite reagents. In this work, a simple, cost-effective, efficient, and automatable method is presented, based on the controlled oxidation of the 5'-terminal alcohol followed by a beta-elimination reaction. The latter reaction leads to the removal of the terminal 5'-nucleoside and subsequent formation of the 5'-phosphate moiety. Thus, chemical phosphorylation of oligonucleotides (DNA or RNA) is achieved without using modified phosphorarnidites.

  DOI：

  10.1021/ol300542s
• 作为产物：
  描述：

  [5-(Diethylamino)-2-formylphenyl] 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate 、 5’-(4,4’-二甲氧基三苯基)-3’-脱氧胸苷 2’-(2-氰乙基-N,N-二异丙基)亚磷酰胺 在 三氯乙酸 、 4,5-二氰基咪唑 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 P-dThd-P-dGuo-P-dThd-P-dThd
  参考文献：
  名称：

  Phosphorylating Reagent-Free Synthesis of 5′-Phosphate Oligonucleotides by Controlled Oxidative Degradation of Their 5′-End

  摘要：

  The 5'-phosphorylated oligonucleotides (5'-pONs) are currently synthesized using expensive and sensitive modified phosphoramidite reagents. In this work, a simple, cost-effective, efficient, and automatable method is presented, based on the controlled oxidation of the 5'-terminal alcohol followed by a beta-elimination reaction. The latter reaction leads to the removal of the terminal 5'-nucleoside and subsequent formation of the 5'-phosphate moiety. Thus, chemical phosphorylation of oligonucleotides (DNA or RNA) is achieved without using modified phosphorarnidites.

  DOI：

  10.1021/ol300542s

文献信息

• Phosphorylating Reagent-Free Synthesis of 5′-Phosphate Oligonucleotides by Controlled Oxidative Degradation of Their 5′-End
  作者：Corinne Sallamand、Audrey Miscioscia、Rémy Lartia、Eric Defrancq

  DOI：10.1021/ol300542s

  日期：2012.4.20

  The 5'-phosphorylated oligonucleotides (5'-pONs) are currently synthesized using expensive and sensitive modified phosphoramidite reagents. In this work, a simple, cost-effective, efficient, and automatable method is presented, based on the controlled oxidation of the 5'-terminal alcohol followed by a beta-elimination reaction. The latter reaction leads to the removal of the terminal 5'-nucleoside and subsequent formation of the 5'-phosphate moiety. Thus, chemical phosphorylation of oligonucleotides (DNA or RNA) is achieved without using modified phosphorarnidites.