TpTpT | 2640-26-8

• 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: TpTpT
• 英文别名: 5'-T3-3'；deoxythymidinyl-[3'→5']-deoxythymidinyl-[3'→5']-deoxythymidine；TTT；3'-TpTpT-5'；O^3'-lin-bis-(5'=>3')thymidylyl-thymidine；O^3'-lin-Bis(5'=>3')thymidylyl-thymidin；thymidylyl-(3'->5')-thymidylyl-(3'->5')-thymidine；5′-d[TTT]-3′；5'-d(TTT)-3'；[(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)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] hydrogen phosphate
• CAS: 2640-26-8
• 化学式: C₃₀H₄₀N₆O₁₉P₂
• 分子量: 850.624
• InChiKey: NHNQSCZKEGUUKX-DNIZJRTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  57
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  328
• 氢给体数：
  7
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  3'-O-acetylthymidine 在 四氮唑 、 对硝基苯酚 、 、 氨 、 水 、 氢气 、 sodium hydride 作用下， 反应 6.0h， 生成 TpTpT
  参考文献：
  名称：

  Helinski, Jan; Dabkowski, Wojciech; Michalski, Jan, Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 76, # 1-4, p. 135 - 138

  摘要：

  DOI：

文献信息

• Oligonucleotide with protected base
  申请人：Ajinomoto Co., Inc.

  公开号：US09371353B2

  公开（公告）日：2016-06-21

  The present invention provides a protected nucleotide for elongation, which can be purified efficiently and in a high yield by a liquid-liquid extraction operation, and can achieve an oligonucleotide production method by a phosphoramidite method. It has been found that the above-mentioned problem can be solved by a particular oligonucleotide comprising a protected base and/or particular oligonucleotide protected by a branched chain-containing aromatic group at 3′-position.

  本发明提供了一种用于延伸的受保护核苷酸，可以通过液液萃取操作高效地和高产率地纯化，并且可以通过磷酰胺酯法实现寡核苷酸的生产方法。已经发现，上述问题可以通过包含受保护碱基和/或在3'-位置含有支链含芳基团的特定寡核苷酸来解决。
• Prebiotic Phosphorylation and Concomitant Oligomerization of Deoxynucleosides to form DNA
  作者：Eddy I. Jiménez、Clémentine Gibard、Ramanarayanan Krishnamurthy

  DOI：10.1002/anie.202015910

  日期：2021.5.3

  RNA and DNA replication, coupled with prebiotic co‐synthesis of deoxyribo‐ and ribo‐nucleotides, have resurrected the hypothesis of co‐emergence of RNA and DNA. As further support, we show that diamidophosphate (DAP) with 2‐aminoimidazole (amido)phosphorylates and oligomerizes deoxynucleosides to form DNA—under conditions similar to those of ribonucleosides. The pyrimidine deoxynucleoside 5′‐O‐amidophosphates

  最近展示的 RNA-DNA 嵌合体 (RDNA) 使 RNA 和 DNA 复制成为可能，再加上脱氧核糖和核糖核苷酸的益生元共合成，重新提出了 RNA 和 DNA 共生的假设。作为进一步的支持，我们表明二酰胺磷酸酯 (DAP) 与 2-氨基咪唑（酰胺基）磷酸化并寡聚化脱氧核苷以形成 DNA——在与核糖核苷相似的条件下。嘧啶脱氧核苷 5'-O-氨基磷酸酯以良好的 (≈60%) 产率形成。有趣的是，嘧啶脱氧核苷（酸）苷的存在增加了嘌呤脱氧核苷酸的产量（≈20%）。同时，观察到寡聚化 (≈18–31%) 主要是 3',5'-磷酸二酯 DNA 键和一些 (<5%) 焦磷酸盐。
• 2-diphenylmethylsilylethyl group as a new protecting group of internucleotidic phosphates in oligonucleotide synthesis
  作者：Shinkichi Honda、Tsujiaki Hata

  DOI：10.1016/s0040-4039(01)93285-x

  日期：1981.1

  Internucleotidic phosphates were protected by 2-diphenylmethylsilylethyl which was selectively removed by treatment with tetrabutylammonium fluoride.

  核苷酸间的磷酸酯被2-二苯基甲基甲硅烷基乙基保护，该2-二苯基甲基甲硅烷基乙基通过用四丁基氟化铵处理选择性地除去。
• Oligonucleotide synthesis by the use of a 2-(levulinyloxymethyl)-5-nitrobenzoyl group as the novel base-labile protecting Group for the 5′-hydroxyl groups of ribonucleoside and 2′-deoxyribonucleoside 3′-phosphoramidites
  作者：Kazuo Kamaike、Hiroaki Takahashi、Takashi Kakinuma、Kimio Morohoshi、Yoshiharu Ishido

  DOI：10.1016/s0040-4039(97)01617-1

  日期：1997.9

  A novel 2-(levulinyloxymethyl)-5-nitrobenzoyl (LMNBz) protecting group for the 5′ position of nucleoside 3′-phosphoramidites was successfully applied to the solid-phase synthesis of both an oligodeoxyribonucleotide (TpTpT and TpTpTpT) and an octaribonucleotide in combination with a 2′-O-Thp protecting group (UpCpApGpUpUpGpG). The LMNBz group was simply unmasked due to its base-labile property by a

  一种新型的2-（乙酰丙酰氧基甲基）-5-硝基苯甲酰基（LMNBz）核苷3'-亚磷酰胺的5'位保护基团已成功地用于寡脱氧核糖核苷酸（TpTpT和TpTpTpTT）和八核糖核苷酸的固相合成带有2'- O -Thp保护基（UpCpApGpUpUpGpG）。LMNBz基团由于其对碱不稳定的特性而通过两步程序（即先用0.5 M的水合肼在1：4的乙酸-吡啶中处理，然后再用0.5 M的咪唑的乙腈处理）简单地将其掩盖。
• BASE-PROTECTED OLIGONUCLEOTIDE
  申请人：AJINOMOTO CO., INC.

  公开号：EP2816053B1

  公开（公告）日：2021-03-24