8-N-(3,5-dimethylphenyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine | 1367203-97-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 8-N-(3,5-dimethylphenyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine
• CAS: 1367203-97-1
• 化学式: C₃₀H₅₀N₆O₃Si₂
• 分子量: 598.936
• InChiKey: RRKMIHUDCPLYMC-RBZQAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.47
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  109.34
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  8-N-(3,5-dimethylphenyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 N-(9-((2R,4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-8-(N-(3,5-dimethylphenyl)acetamido)-9H-purin-6-yl)benzamide
  参考文献：
  名称：

  Synthesis of C8-Arylamine-Modified 2′-Deoxyadenosine Phosphoramidites and their Site-Specific Incorporation into Oligonucleotides

  摘要：

  AbstractAdducts of C8‐(N‐acetyl)‐arylamines and 2′‐deoxyadenosine were synthesised by palladium‐catalysed CN cross‐coupling chemistry. These 2′‐dA adducts were converted into the corresponding 3′‐phosphoramidites and site‐specifically incorporated into DNA oligonucleotides, which were characterised by mass spectrometry, UV thermal‐stability assays and circular dichroism. These modified oligonucleotides were also used in EcoRI restriction assays and in primer‐extension studies with three different DNA polymerases. The incorporation of the 2′‐dA lesion close to the EcoRI restriction site dramatically reduced the susceptibility of the DNA strand to cleavage; this indicates a significant local distortion of the DNA double helix. The incorporation of the acetylated C8‐2′‐dA‐phosphoramidites into 20‐mer oligonucleotides failed, however, because the N‐acetyl group was lost during the deprotection process. Instead the corresponding C8‐NH‐2′‐dA‐modified oligonucleotides were obtained. The effect of the C8‐NH‐arylamine‐dA lesion on the replication by DNA polymerases was clearly dependent both on the polymerase used and on the arylamine‐dA damage.

  DOI：

  10.1002/cbic.201100573
• 作为产物：
  描述：

  2'-脱氧腺苷 在 吡啶 、 咪唑 、 tris-(dibenzylideneacetone)dipalladium(0) 、 溴 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 乙二醇二甲醚 为溶剂， 反应 32.0h， 生成 8-N-(3,5-dimethylphenyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine
  参考文献：
  名称：

  Synthesis of C8-Arylamine-Modified 2′-Deoxyadenosine Phosphoramidites and their Site-Specific Incorporation into Oligonucleotides

  摘要：

  AbstractAdducts of C8‐(N‐acetyl)‐arylamines and 2′‐deoxyadenosine were synthesised by palladium‐catalysed CN cross‐coupling chemistry. These 2′‐dA adducts were converted into the corresponding 3′‐phosphoramidites and site‐specifically incorporated into DNA oligonucleotides, which were characterised by mass spectrometry, UV thermal‐stability assays and circular dichroism. These modified oligonucleotides were also used in EcoRI restriction assays and in primer‐extension studies with three different DNA polymerases. The incorporation of the 2′‐dA lesion close to the EcoRI restriction site dramatically reduced the susceptibility of the DNA strand to cleavage; this indicates a significant local distortion of the DNA double helix. The incorporation of the acetylated C8‐2′‐dA‐phosphoramidites into 20‐mer oligonucleotides failed, however, because the N‐acetyl group was lost during the deprotection process. Instead the corresponding C8‐NH‐2′‐dA‐modified oligonucleotides were obtained. The effect of the C8‐NH‐arylamine‐dA lesion on the replication by DNA polymerases was clearly dependent both on the polymerase used and on the arylamine‐dA damage.

  DOI：

  10.1002/cbic.201100573