5'-d((8-Br-G)C)-3' | 1257514-31-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （3'->5'）-二核苷酸和类似物
• 英文名称: 5'-d((8-Br-G)C)-3'
• 英文别名: br8Gua-dRibf-P-dCyd；[(2R,3S,5R)-5-(2-amino-8-bromo-6-oxo-1H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] [(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl hydrogen phosphate
• CAS: 1257514-31-0
• 化学式: C₁₉H₂₄BrN₈O₁₀P
• 分子量: 635.325
• InChiKey: MICLJJBCNIFFOG-DARWFRJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  259
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5'-d((8-Br-G)C)-3' 、 4-苄氧基苯硼酸 在 triphenylphosphine trisulfonate 、 palladium diacetate 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以60%的产率得到5'-d((G-8-(p-OBnPh))C)-3'
  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

文献信息

• Postsynthetic Guanine Arylation of DNA by Suzuki−Miyaura Cross-Coupling
  作者：Alireza Omumi、Daniel G. Beach、Michael Baker、Wojciech Gabryelski、Richard A. Manderville

  DOI：10.1021/ja106158b

  日期：2011.1.12

  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.