1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-3-(2-propynyl)thymine | 1012306-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-3-(2-propynyl)thymine
• 英文别名: 5'-O-DMT-N²-propargylthymidine；1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-5-methyl-3-prop-2-ynylpyrimidine-2,4-dione
• CAS: 1012306-26-1
• 化学式: C₃₄H₃₄N₂O₇
• 分子量: 582.653
• InChiKey: LWVKPIOIYVMLER-OJDZSJEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-3-(2-propynyl)thymine 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 以97%的产率得到N-(3-propargyl)thymidine
  参考文献：
  名称：

  Triazole-Linked Dumbbell Oligodeoxynucleotides with NF-κB Binding Ability as Potential Decoy Molecules

  摘要：

  [Graphics]Triazole-cross-linked oligodeoxynucleotides were synthesized with use of the Cu(I) catalyzed alkyne-azide cycloaddition (CuAAC) with oligodeoxynucleotides possessing N-3-(azidoethyl)thymidine and N-3-(propargyl)thymidine at the 3'- and 5'-termini. The newly synthesized oligodeoxynucleotides were thermally stable and their global structures retained those of non-cross-linked oligodeoxynucleotides. The newly synthesized dumbbell oligodeoxynucleotides showed excellent stability against snake venom phosphodiesterase (3'-exonuclease) and high thermal stability, which are necessary for decoy molecules to achieve biological responses leading to alteration of gene expression. Moreover; dumbbell oligodeoxynucleotides have the ability to bind to NF-kappa B p50 homodimer within a similar range to that of a control double-stranded decoy olicodeoxynucleotide. This strategy allows us to prepare triazole-linked dumbbell oligodeoxynucleotides with a range of loop lengths, and we found that the greater the number of the thymidine residues constituting the loop region, the higher the binding affinity of the dumbbell oligodeoxynucleotides to the nuclear factor kappa B. This means that a protein binding ability of the dumbbell oligodeoxynucleotides could be modulated by altering the loop size. This study clearly shows that cross-linking by the triazole Structure does not prevent the dumbbell oligodeoxynucleotides from binding to the nuclear factor kappa B transcription factor. Therefore, the results obtained conclusively demonstrate that the triazole cross-linked dumbbell oligodeoxynucleotides could be proposed as powerful decoy molecules.

  DOI：

  10.1021/jo702459b
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 在 吡啶 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-3-(2-propynyl)thymine
  参考文献：
  名称：

  稳定的叠氮化物和炔烃官能化的亚磷酰胺核苷的合成。

  摘要：

  叠氮化物与用于自动寡核苷酸合成的亚磷酰胺的不相容性限制了使用CuAAC化学交联和稳定寡核苷酸的方法。在本文中，我们报道了优化的反应条件以合成胸苷和胞苷亚磷酰胺的叠氮化物衍生物。在室温下使用31 P NMR对新型亚磷酰胺的稳定性进行研究，结果表明6小时后降解率不到10％。叠氮化物修饰的胸苷已成功地用作DNA序列标准亚磷酰胺合成中的内部修饰剂。嘧啶的合成的叠氮化物和炔烃衍生物将允许叠氮化物和炔烃点击对有效地掺入核酸，因此拓宽了点击化学在研究核酸化学中的适用性。

  DOI：

  10.1016/j.tetlet.2018.12.018

文献信息

• Tris(azidoethyl)amine Hydrochloride; a Versatile Reagent for Synthesis of Functionalized Dumbbell Oligodeoxynucleotides
  作者：Satoshi Ichikawa、Hideaki Ueno、Takuya Sunadome、Kousuke Sato、Akira Matsuda

  DOI：10.1021/ol400001w

  日期：2013.2.1

  Triazole-cross-linked oligodeoxynucleotides were synthesized using the Cu(I) catalyzed allryne-azide cycloaddition with tris(azidoethyl)amine hydrochloride and oligodeoxynucleotides possessing N-3-(propargyl)thymidine at both the 3'- and 5'-terminl. Further installation of a functional molecule to the dumbbell oligodeoxynucleotides was achieved by utilizing the remaining azide group.
• Synthesis of stable azide and alkyne functionalized phosphoramidite nucleosides
  作者：Suresh Lingala、Lars Ulrik Nordstrøm、Prabodhika R. Mallikaratchy

  DOI：10.1016/j.tetlet.2018.12.018

  日期：2019.1

  stabilize oligonucleotides has been limited by the incompatibility of azides with the phosphoramidites used in automated oligonucleotide synthesis. Herein we report optimized reaction conditions to synthesize azide derivatives of thymidine and cytidine phosphoramidites. Investigation of the stability of the novel phosphoramidites using 31P NMR at room temperature showed less than 10% degradation after 6 hours

  叠氮化物与用于自动寡核苷酸合成的亚磷酰胺的不相容性限制了使用CuAAC化学交联和稳定寡核苷酸的方法。在本文中，我们报道了优化的反应条件以合成胸苷和胞苷亚磷酰胺的叠氮化物衍生物。在室温下使用31 P NMR对新型亚磷酰胺的稳定性进行研究，结果表明6小时后降解率不到10％。叠氮化物修饰的胸苷已成功地用作DNA序列标准亚磷酰胺合成中的内部修饰剂。嘧啶的合成的叠氮化物和炔烃衍生物将允许叠氮化物和炔烃点击对有效地掺入核酸，因此拓宽了点击化学在研究核酸化学中的适用性。
• Triazole-Linked Dumbbell Oligodeoxynucleotides with NF-κB Binding Ability as Potential Decoy Molecules
  作者：Masanori Nakane、Satoshi Ichikawa、Akira Matsuda

  DOI：10.1021/jo702459b

  日期：2008.3.1

  [Graphics]Triazole-cross-linked oligodeoxynucleotides were synthesized with use of the Cu(I) catalyzed alkyne-azide cycloaddition (CuAAC) with oligodeoxynucleotides possessing N-3-(azidoethyl)thymidine and N-3-(propargyl)thymidine at the 3'- and 5'-termini. The newly synthesized oligodeoxynucleotides were thermally stable and their global structures retained those of non-cross-linked oligodeoxynucleotides. The newly synthesized dumbbell oligodeoxynucleotides showed excellent stability against snake venom phosphodiesterase (3'-exonuclease) and high thermal stability, which are necessary for decoy molecules to achieve biological responses leading to alteration of gene expression. Moreover; dumbbell oligodeoxynucleotides have the ability to bind to NF-kappa B p50 homodimer within a similar range to that of a control double-stranded decoy olicodeoxynucleotide. This strategy allows us to prepare triazole-linked dumbbell oligodeoxynucleotides with a range of loop lengths, and we found that the greater the number of the thymidine residues constituting the loop region, the higher the binding affinity of the dumbbell oligodeoxynucleotides to the nuclear factor kappa B. This means that a protein binding ability of the dumbbell oligodeoxynucleotides could be modulated by altering the loop size. This study clearly shows that cross-linking by the triazole Structure does not prevent the dumbbell oligodeoxynucleotides from binding to the nuclear factor kappa B transcription factor. Therefore, the results obtained conclusively demonstrate that the triazole cross-linked dumbbell oligodeoxynucleotides could be proposed as powerful decoy molecules.