O⁶-benzyl-8N-(4-biphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine | 919530-62-4

• 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: O⁶-benzyl-8N-(4-biphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine
• 英文别名: 9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-6-phenylmethoxy-8-N-(4-phenylphenyl)purine-2,8-diamine
• CAS: 919530-62-4
• 化学式: C₄₁H₅₆N₆O₄Si₂
• 分子量: 753.104
• InChiKey: LTOKTQIQSMVRBN-LBFZIJHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  53
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  O⁶-benzyl-8N-(4-biphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine 在 钯 氢气 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 8-((1,1'-联苯)-4-基氨基)-2'-脱氧鸟苷
  参考文献：
  名称：

  诱变/致癌氨基或硝基芳烃化学合成2'-脱氧鸟苷-C8加合物的实用方法

  摘要：

  利用钯介导的受保护的8-氨基-dG与溴代芳烃的交叉偶联反应，开发了合成具有几种致突变和致癌的氨基或硝基芳烃的2'-脱氧鸟苷-C8（dG-C8）加合物的合成方法。大约80％的收率，然后进行常规的脱保护程序。该方法可用于制备各种带有氨基或硝基芳烃的可靠的dG-C8加合物。

  DOI：

  10.1016/s0040-4039(03)01484-9
• 作为产物：
  描述：

  6-Benzyloxy-N8-biphenyl-4-yl-N2-[bis-(4-methoxy-phenyl)-phenyl-methyl]-9-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9H-purine-2,8-diamine 在 zinc dibromide 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 生成 O⁶-benzyl-8N-(4-biphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine
  参考文献：
  名称：

  诱变/致癌氨基或硝基芳烃化学合成2'-脱氧鸟苷-C8加合物的实用方法

  摘要：

  利用钯介导的受保护的8-氨基-dG与溴代芳烃的交叉偶联反应，开发了合成具有几种致突变和致癌的氨基或硝基芳烃的2'-脱氧鸟苷-C8（dG-C8）加合物的合成方法。大约80％的收率，然后进行常规的脱保护程序。该方法可用于制备各种带有氨基或硝基芳烃的可靠的dG-C8加合物。

  DOI：

  10.1016/s0040-4039(03)01484-9

文献信息

• Synthesis of DNA Strands Site-Specifically Damaged by C8-Arylamine Purine Adducts and Effects on Various DNA Polymerases
  作者：Nicolas Böge、Maike I. Jacobsen、Zita Szombati、Sabrina Baerns、Francesca Di Pasquale、Andreas Marx、Chris Meier

  DOI：10.1002/chem.200800979

  日期：2008.12.8

  C8-Arylamine-dG and C8-arylamine-dA adducts have been prepared using palladium cross-coupling chemistry. These adducts were subsequently converted into the corresponding 5'-O-DMTr-C8-arylamine-3'-O-phosphoramidites and then used for the automated synthesis of different site-specifically modified oligonucleotides. These "damaged" oligonucleotides have been characterized by ESI-MS, UV thermal stability

  使用钯交叉偶联化学已经制备了C8-芳胺-dG和C8-芳基胺-dA加合物。随后将这些加合物转化为相应的5'-O-DMTr-C8-芳基胺-3'-O-亚磷酰胺，然后用于自动合成不同的位点特异性修饰的寡核苷酸。这些“损坏”的寡核苷酸已通过ESI-MS，UV热稳定性测定和圆二色性进行了表征，它们已用于EcoRI测定以及使用各种DNA聚合酶的引物延伸研究中。
• Synthesis of DNA-Oligonucleotides Damaged by Arylamine-Modified 2′-Deoxyguanosine
  作者：N. Böge、Z. Szombati、C. Meier

  DOI：10.1080/15257770701490738

  日期：2007.11.26

  C8-Arylamine-dG adducts bearing a labile N-formamidine group at the exocyclic amino function were converted into their corresponding 5'-O-DMTr-3'-0-phosphoramidite-C8-arylamine-dG derivatives. These compounds were used for the automated synthesis of site-specifically modified oligonucleotides. These oligonucleotides were characterized by ESI-MS and enzymatic digestion and studied for their CD properties and T-m values.
• Synthesis and Properties of Oligonucleotides Containing C8-Deoxyguanosine Arylamine Adducts of Borderline Carcinogens
  作者：Nicolas Böge、Sonja Gräsl、Chris Meier

  DOI：10.1021/jo061803t

  日期：2006.12.1

  C8-Arylamine-dG adducts of borderline carcinogens and the bladder and breast carcinogen 4-amino-biphenyl were prepared using cross-coupling chemistry. These adducts were converted into the corresponding C8-arylamine-5'-O-DMTr-2'-deoxyguanosine phosphoramidites and then used as building blocks for automated synthesis of site-specifically modified oligonucleotides. The oligonucleotides were characterized by UV melting temperature analysis, enzymatic digestion, and circular dichroism.
• A practical approach for the chemical synthesis of 2′-deoxyguanosine-C8 adducts with mutagenic/carcinogenic amino- or nitro-arenes
  作者：Takeji Takamura-Enya、Satoko Ishikawa、Masataka Mochizuki、Keiji Wakabayashi

  DOI：10.1016/s0040-4039(03)01484-9

  日期：2003.8

  of 2′-deoxyguanosine-C8 (dG-C8) adducts with several mutagenic and carcinogenic amino- or nitro-arenes were developed using the palladium-mediated cross-coupling reaction of protected 8-amino-dG with bromoarenes in around 80% yields, followed by conventional deprotection procedures. This approach can be applied to preparation of a variety of authentic dG-C8 adducts with amino or nitro-arenes.

  利用钯介导的受保护的8-氨基-dG与溴代芳烃的交叉偶联反应，开发了合成具有几种致突变和致癌的氨基或硝基芳烃的2'-脱氧鸟苷-C8（dG-C8）加合物的合成方法。大约80％的收率，然后进行常规的脱保护程序。该方法可用于制备各种带有氨基或硝基芳烃的可靠的dG-C8加合物。