5'-O-Phosphoryl-thymidylyl-(3'-5')-thymidylyl-(3'-5')-thymidin | 1820-78-6

• 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: 5'-O-Phosphoryl-thymidylyl-(3'-5')-thymidylyl-(3'-5')-thymidin
• 英文别名: 5'-O-Phosphoryl-thymidylyl-(3'-5')-thymidylyl-(3'-5')-thymidin, Thymidylyl-(5'-3')-thymidylyl-(5'-3')-thymidin-5'-phosphat；pTpTpT；[(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]methyl [(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-(phosphonooxymethyl)oxolan-3-yl] hydrogen phosphate
• CAS: 1820-78-6
• 化学式: C₃₀H₄₁N₆O₂₂P₃
• 分子量: 930.604
• InChiKey: WUURCCCLYPVEDU-DNIZJRTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.8
• 重原子数：
  61
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  374
• 氢给体数：
  8
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  胸苷酸 在 sodium hydroxide 、 2,2'-二硫二吡啶 、 三苯基膦 作用下， 以 吡啶 为溶剂， 反应 3.33h， 生成 5'-O-Phosphoryl-thymidylyl-(3'-5')-thymidylyl-(3'-5')-thymidin
  参考文献：
  名称：

  使用 o,o'-二氨基二苯基保护脱氧核糖寡核苷酸的 5'-末端磷酸盐

  摘要：

  以三苯基膦和 2,2'-二硫化二吡啶为缩合剂，制备了 5'-磷酸核苷的环状磷酰二胺衍生物，用于合成寡脱氧核糖核苷酸。通过将 AgOAc 和酸酐共加成到常规体系 iAmONO-吡啶-AcOH 中，显着加速了二氨基的去除。

  DOI：

  10.1246/cl.1984.175

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.
• PROTECTION OF 5′-TERMINAL PHOSPHATE OF DEOXYRIBOOLIGONUCLEOTIDES BY USE OF o,o′-DIAMINOBIPHENYL
  作者：Makoto Nishizawa、Takashi Kurihara、Tsujiaki Hata

  DOI：10.1246/cl.1984.175

  日期：1984.2.5

  Cyclic phosphorodianilidate derivatives of nucleoside 5′-phosphates were prepared by use of triphenylphosphine and 2,2′-dipyridyl disulfide as condensing agent and used for the synthesis of oligodeoxyribonucleotides. Removal of the diamino group was remarkably accelerated by coaddition of AgOAc and acid anhydrides to the conventional system, iAmONO-pyridine-AcOH.

  以三苯基膦和 2,2'-二硫化二吡啶为缩合剂，制备了 5'-磷酸核苷的环状磷酰二胺衍生物，用于合成寡脱氧核糖核苷酸。通过将 AgOAc 和酸酐共加成到常规体系 iAmONO-吡啶-AcOH 中，显着加速了二氨基的去除。