N(3)-Allyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)thymidine | 150884-11-0

• 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: N(3)-Allyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)thymidine
• 英文别名: 1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[tert-butyl(dimethyl)silyl]oxyoxolan-2-yl]-5-methyl-3-prop-2-enylpyrimidine-2,4-dione
• CAS: 150884-11-0
• 化学式: C₄₀H₅₀N₂O₇Si
• 分子量: 698.932
• InChiKey: ZADJHIXKXAXNDK-LIVOIKKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.21
• 重原子数：
  50
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  86.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N(3)-Allyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)thymidine 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 3.5h， 生成
  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：

  O⁴-Allyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)thymidine 在 四(三苯基膦)钯 diethylammonium hydrogencarbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.08h， 生成 N(3)-Allyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)thymidine
  参考文献：
  名称：

  O-Allyl protection of guanine and thymine residues in oligodeoxyribonucleotides

  摘要：

  DOI：

  10.1021/jo00072a050

文献信息

• O-Allyl protection of guanine and thymine residues in oligodeoxyribonucleotides
  作者：Yoshihiro Hayakawa、Masaaki Hirose、Ryoji Noyori

  DOI：10.1021/jo00072a050

  日期：1993.9
• 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.