N2-isobutyryl-8-(4''-benzyloxyphenyl)-2'-deoxyguanosine | 1257514-40-1

• 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: N2-isobutyryl-8-(4''-benzyloxyphenyl)-2'-deoxyguanosine
• CAS: 1257514-40-1
• 化学式: C₂₇H₂₉N₅O₆
• 分子量: 519.557
• InChiKey: CFRJSXZKTGCDFO-PWRODBHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  151.59
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N2-isobutyryl-8-(4''-benzyloxyphenyl)-2'-deoxyguanosine 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 作用下， 反应 5.0h， 以79%的产率得到5'-O-(4,4'-dimethoxytrityl)-N2-isobutyryl-8-(4''-benzyloxyphenyl)-2'-deoxyguanosine
  参考文献：
  名称：

  Postsynthetic Guanine Arylation of DNA by Suzuki−Miyaura Cross-Coupling

  摘要：

  Direct radical addition reactions at the C-8-site of 2'-deoxyguanosine (dG) can afford C-8-Ar-dG adducts that are produced by carcinogenic arylhydrazines, polycyclic aromatic hydrocarbons, and certain phenolic toxins. Such modified nucleobases are also highly fluorescent for sensing applications and possess useful electron transfer properties. The site-specific synthesis of oligonucleotides containing the C-8-Ar-G adduct can be problematic. These lesions are sensitive to acids and oxidants that are commonly used in solid-phase DNA synthesis and are too bulky to be accepted as substrates for enzymatic synthesis by DNA polymerases. Using the Suzuki-Miyaura cross-coupling reaction, we have synthesized a number of C-8-Ar-G-modified oligonucleotides (dimers, trimers, decamers, and a 15-mer) using a range of arylboronic acids. Good to excellent yields were obtained, and the reaction is insensitive to the nature of the bases flanking the convertible 8-Br-G nucleobase, as both pyrimidines and purines are tolerated. The impact of the C-8-Ar-G lesion was also characterized by electrospray ionization tandem mass spectrometry, UV melting temperature analysis, circular dichroism, and fluorescence spectroscopy. The C-8-Ar-G-modified oligonucleotides are expected to be useful substrates for diagnostic applications and understanding the biological impact of the C-8-Ar-G lesion.

  DOI：

  10.1021/ja106158b
• 作为产物：
  描述：

  8-溴-2'-脱氧鸟苷 在 吡啶 、 三甲基氯硅烷 、 triphenylphosphine trisulfonate 、 palladium diacetate 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 生成 N2-isobutyryl-8-(4''-benzyloxyphenyl)-2'-deoxyguanosine
  参考文献：
  名称：

  Postsynthetic Guanine Arylation of DNA by Suzuki−Miyaura Cross-Coupling

  摘要：

  Direct radical addition reactions at the C-8-site of 2'-deoxyguanosine (dG) can afford C-8-Ar-dG adducts that are produced by carcinogenic arylhydrazines, polycyclic aromatic hydrocarbons, and certain phenolic toxins. Such modified nucleobases are also highly fluorescent for sensing applications and possess useful electron transfer properties. The site-specific synthesis of oligonucleotides containing the C-8-Ar-G adduct can be problematic. These lesions are sensitive to acids and oxidants that are commonly used in solid-phase DNA synthesis and are too bulky to be accepted as substrates for enzymatic synthesis by DNA polymerases. Using the Suzuki-Miyaura cross-coupling reaction, we have synthesized a number of C-8-Ar-G-modified oligonucleotides (dimers, trimers, decamers, and a 15-mer) using a range of arylboronic acids. Good to excellent yields were obtained, and the reaction is insensitive to the nature of the bases flanking the convertible 8-Br-G nucleobase, as both pyrimidines and purines are tolerated. The impact of the C-8-Ar-G lesion was also characterized by electrospray ionization tandem mass spectrometry, UV melting temperature analysis, circular dichroism, and fluorescence spectroscopy. The C-8-Ar-G-modified oligonucleotides are expected to be useful substrates for diagnostic applications and understanding the biological impact of the C-8-Ar-G lesion.

  DOI：

  10.1021/ja106158b