8-N-(4-methoxyphenyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine | 1062513-32-9

• 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-(4-methoxyphenyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine
• CAS: 1062513-32-9
• 化学式: C₂₉H₄₈N₆O₄Si₂
• 分子量: 600.909
• InChiKey: PFTIECFKNQNXRG-YTFSRNRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.86
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  118.57
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  8-N-(4-methoxyphenyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 N-(9-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-8-(N-(4-methoxyphenyl)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-(4-methoxyphenyl)-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

文献信息

• Synthesis of C8-Modified 2″-Deoxyadenosine with Carcinogenic Arylamines
  作者：M. I. Jacobsen、C. Meier

  DOI：10.1080/15257770701527976

  日期：2007.11.26

  The synthesis of phosphoramidites of C8-modified 2'-deoxyadenosine with carcinogenic arylamines p-anisidine and 4-aminobiphenyl is described. Two different methods were studied related to the glycon and base protection groups.

  描述了C8-修饰的2'-脱氧腺苷与致癌性芳胺对-茴香胺和4-氨基联苯的亚磷酰胺的合成。研究了两种与糖基和碱基保护基有关的不同方法。