5'-TTT-TT-3' | 17708-74-6

• 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'-TTT-TT-3'
• 英文别名: single-stranded dT5；[(2R,3S,5R)-3-[hydroxy-[[(2R,3S,5R)-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]oxy-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: 17708-74-6
• 化学式: C₅₀H₆₆N₁₀O₃₃P₄
• 分子量: 1459.02
• InChiKey: SNTINBZZQZEOPH-OPOFJALESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.9
• 重原子数：
  97
• 可旋转键数：
  26
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  557
• 氢给体数：
  11
• 氢受体数：
  33

反应信息

• 作为反应物：
  描述：

  5'-TTT-TT-3' 、 疊氮乙酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 C₅₂H₆₇N₁₃O₃₄P₄
  参考文献：
  名称：

  Sensor with a scaffold having changeable conformations

  摘要：

  这项发明涉及一种具有包含药物的容器的支架传感器，用于触发药物释放，其中支架在本质上构象亚稳，并提供了一种制造方法。

  公开号：

  US09758545B2
• 作为产物：
  描述：

  3’-O-(4,4’-二甲氧基三苯甲基)胸苷 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 5'-TTT-TT-3'
  参考文献：
  名称：

  核苷酸，第 LXV 部分，2'-脱氧核糖核苷 5'-亚磷酰胺的合成：反向 (5'-3')-寡核苷酸方法的新构件

  摘要：

  The syntheses of the 3'-O-(4,4'-dimethoxytrityl)-protected 5'-phosphoramidites 25-28 and 5'-(hydrogen succinates) 29-32, which can be used as monomeric building blocks for the inverse (5'-3')-oligodeoxyribonucleotide synthesis are described (Scheme). These activated nucleosides and nucleotides were obtained by two slightly different four-step syntheses starting with the base-protected nucleosides 13-20. For the protection of the aglycon residues, the well-established 2-(4-nitrophenyl)ethyl (npe) and [2-(4-nitrophenyl)ethoxy]carbonyl (npeoc) groups were used. The assembly of the oligonucleotides required a slightly increased coupling time of 3 min in application of the common protocol (see Table 1). The use of pyridinium hydrochloride as an activator (instead of 1H-tetrazole) resulted in an extremely shorter activation time of 30 seconds. We established the efficiency of this inverse strategy by the synthesis of the oligonucleotide 3'-conjugates 33 and 34 which carry lipophilic caps derived from cholesterol and vitamin E, respectively, as well as by the formation of (3'-3')- and (5'-5')-internucleotide linkages (see Table 2).

  DOI：

  10.1002/1522-2675(20000809)83:8<2023::aid-hlca2023>3.0.co;2-p

文献信息

• Design, Synthesis, and Cellular Uptake of Oligonucleotides Bearing Glutathione-Labile Protecting Groups
  作者：Hisao Saneyoshi、Takayuki Ohta、Yuki Hiyoshi、Takeo Saneyoshi、Akira Ono

  DOI：10.1021/acs.orglett.8b03501

  日期：2019.2.15

  Glutathione-labile protecting groups for phosphodiester moieties in oligonucleotides were designed, synthesized, and incorporated into oligonucleotides. The protecting groups on the phosphodiester moieties were cleaved in a buffer containing 10 mM glutathione, which was used as a model of intracellular fluid. Cellular uptake of oligonucleotides bearing glutathione-labile protecting groups was strongly affected

  设计，合成并合成寡核苷酸中对寡核苷酸中的磷酸二酯部分的谷胱甘肽不稳定的保护基。在含有10mM谷胱甘肽的缓冲液中裂解磷酸二酯部分上的保护基，该缓冲液用作细胞内液的模型。带有谷胱甘肽不稳定的保护基的寡核苷酸的细胞摄取受到保护基团的位置和数量的强烈影响。
• 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。
• Synthesis of oligodeoxynucleotides using the oxidatively cleavable 4-methoxytritylthio (MMTrS) group for protection of the 5′-hydroxyl group
  作者：Kohji Seio、Miyuki Shiraishi、Eri Utagawa、Akihiro Ohkubo、Mitsuo Sekine

  DOI：10.1039/b9nj00678h

  日期：——

  We examined the synthesis of oligodeoxynucleotides containing all four nucleobases using the 4-methoxytritylthio (MMTrS) group for protection of the 5′-hydroxyl group. The MMTrS group could be introduced into 3′-O-TBDMS-deoxycytidine, -deoxyadenosine and -deoxyguanosine with the appropriate base protecting groups using strong bases such as n-butyl lithium and lithium hexamethyldisilazide. Because the

  我们使用4-甲氧基三苯甲基硫基（MMTrS）基团来保护5'-羟基，研究了包含所有四个核碱基的寡脱氧核苷酸的合成。MMTrS组可以引入3'- O -TBDMS-脱氧胞苷， -脱氧腺苷 和 -脱氧鸟苷 带有适当的碱保护基团，并使用强碱，例如 正丁基锂 和 六甲基二硅叠氮化锂。因为MMTrS基团可通过用I 2水溶液氧化而除去，所以核苷酸间的氧化亚磷酸酯中间体可以同时进行。因此，核苷酸链可以以包括偶联，加帽和氧化/脱保护的三步方案进行延伸。可以使用此协议合成具有10和20个混合碱基序列的寡脱氧核苷酸。
• Bioreductive deprotection of 4-nitrobenzyl group on thymine base in oligonucleotides for the activation of duplex formation
  作者：Hisao Saneyoshi、Yuki Hiyoshi、Koichi Iketani、Kazuhiko Kondo、Akira Ono

  DOI：10.1016/j.bmcl.2015.10.025

  日期：2015.12

  Oligonucleotides containing 4-O-(4-NO2-benzyl)thymine residues were synthesized to assess potential prodrug-type action against hypoxic cells. These modified oligonucleotides were incapable of stable duplex formation under non-hypoxic conditions. However, following deprotection of the thymine residues under bioreductive conditions, the deprotected oligonucleotides were able to form stable duplexes with target oligonucleotides. (C) 2015 Elsevier Ltd. All rights reserved.
• MAKINO, KEISUKE;MURAKAMI, AKIRA;NAGAHARA, SHUNJI;NAKATSUJI, YUNA;TAKEUCHI+, 15TH SYMP. NUCL. ACIDS CHEM., SAPPORO, SEPT. 19TH - 21ST, 1988, OXFORD; W+
  作者：MAKINO, KEISUKE、MURAKAMI, AKIRA、NAGAHARA, SHUNJI、NAKATSUJI, YUNA、TAKEUCHI+

  DOI：——

  日期：——