2'-Deoxy-O⁶-<(p-nitrophenyl)ethyl>-N²-(1-pyrenylmethyl)guanosine | 132209-52-0

• 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: 2'-Deoxy-O⁶-<(p-nitrophenyl)ethyl>-N²-(1-pyrenylmethyl)guanosine
• 英文别名: N²-(1-pyrenylmethyl)-O⁶-(p-nitrophenylethyl)-2'-deoxyguanosine；N²-(1-pyrenylmethyl)-O⁶-(2-(4-nitrophenyl)ethyl)-2′-deoxyguanosine；(2R,3S,5R)-2-(hydroxymethyl)-5-[6-[2-(4-nitrophenyl)ethoxy]-2-(pyren-1-ylmethylamino)purin-9-yl]oxolan-3-ol
• CAS: 132209-52-0
• 化学式: C₃₅H₃₀N₆O₆
• 分子量: 630.66
• InChiKey: PSZMYZFLIIAYRQ-ZGIBFIJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  47.0
• 可旋转键数：
  10.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  157.69
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2'-Deoxy-O⁶-<(p-nitrophenyl)ethyl>-N²-(1-pyrenylmethyl)guanosine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 吡啶 为溶剂， 生成 (+/-)-N²-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)guanosine phosphoramidite
  参考文献：
  名称：

  在脱氧鸟苷和脱氧腺苷的氨基官能团上烷基化的多环芳香烃核苷酸和寡核苷酸加合物的合成

  摘要：

  描述了具有连接至脱氧鸟苷和脱氧腺苷的环外氨基官能团的烃部分的1-苯甲基甲基单核苷加合物的有效合成。

  DOI：

  10.1016/s0040-4039(00)97168-5
• 作为产物：
  描述：

  1-芘甲醛 在 羟胺 、 溶剂黄146 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2'-Deoxy-O⁶-<(p-nitrophenyl)ethyl>-N²-(1-pyrenylmethyl)guanosine
  参考文献：
  名称：

  在脱氧鸟苷和脱氧腺苷的氨基官能团上烷基化的多环芳香烃核苷酸和寡核苷酸加合物的合成

  摘要：

  描述了具有连接至脱氧鸟苷和脱氧腺苷的环外氨基官能团的烃部分的1-苯甲基甲基单核苷加合物的有效合成。

  DOI：

  10.1016/s0040-4039(00)97168-5

文献信息

• Synthesis of <i>N</i>²-Deoxyguanosine Modified DNAs and the Studies on Their Translesion Synthesis by the <i>E. coli</i> DNA Polymerase IV
  作者：Pratibha P. Ghodke、Praneeth Bommisetti、Deepak T. Nair、P. I. Pradeepkumar

  DOI：10.1021/acs.joc.8b02082

  日期：2019.2.15

  We report the synthesis of N2-aryl (benzyl, naphthyl, anthracenyl, and pyrenyl)-deoxyguanosine (dG) modified phosphoramidite building blocks and the corresponding damaged DNAs. Primer extension studies using E. coli Pol IV, a translesion polymerase, demonstrate that translesion synthesis (TLS) across these N2-dG adducts is error free. However, the efficiency of TLS activity decreases with increase

  我们报告了N2-芳基（苄基，萘基，蒽基和pyr基）-脱氧鸟苷（dG）修饰的亚磷酰胺结构单元和相应的受损DNA的合成。使用大肠埃希氏大肠杆菌Pol IV（一种跨病变聚合酶）进行引物延伸研究表明，跨这些N2-dG加合物的跨病变合成（TLS）是没有错误的。然而，TLS活性的效率随着加合物的空间体积的增加而降低。受损的DNA-Pol IV复合物的分子动力学模拟揭示了酶和加合物的关键氨基酸残基（Phe13，Ile31，Gly32，Gly33，Ser42，Pro73，Gly74，Phe76和Tyr79）之间的范德华相互作用疏水性口袋中的大块损坏，有利于TLS。总体而言，此处给出的结果为Pol IV对N2-芳基-dG受损DNA上的TLS提供了见解。
• Synthesis of Oligonucleotide Adducts of the Bay Region Diol Epoxide Metabolites of Carcinogenic Polycyclic Aromatic Hydrocarbons
  作者：Hongmee Lee、Ernestina Luna、Michael Hinz、John J. Stezowski、Alexander S. Kiselyo、Ronald G. Harvey

  DOI：10.1021/jo00122a048

  日期：1995.9

  An efficient method for the site-specific synthesis of adducts between the biologically active diol epoxide metabolites of carcinogenic polycyclic aromatic hydrocarbons (PAHs) and oligonucleotides in which a PAH component of predetermined stereochemistry is linked covalently to the exocyclic amino groups of deoxyadenosine (dA) and deoxyguanosine (dG) is described. The synthetic strategy involves in the key step coupling a protected halopurine derivative with an amino derivative (or an aminotriol derivative) of the PAH. This method was initially employed to prepare the dA and dG adducts of the model PAH 1-methylpyrene. The appropriately protected dA adduct was then incorporated into the oligonucleotide sequence d(GCAGGTCA(*)AGAG) where A(*) represents N6-pyrenylmethyl-dA. This methodology was extended to the synthesis of trans adducts of anti-diol epoxide metabolites of benzo[a]pyrene and 5-methylchrysene linked to the 6-amino function of dA. The parent hydrocarbons are widespread environmental carcinogens. This synthetic approach, dubbed the total synthesis method, complements the direct synthesis method which involves the direct reaction of PAH diol epoxides with oligonucleotides. The total synthesis method is broader in scope than the latter, and it is readily adaptable to the large scale preparation of PAH-oligonucleotide adducts required for structure determination by high resolution NMR and X-ray crystallographic techniques.
• LEE, HONGMEE;HINZ, MICHAEL;STEZOWSKI, JOHN J.;HARVEY, RONALD G., TETRAHEDRON LETT., 31,(1990) N7, C. 6773-6776
  作者：LEE, HONGMEE、HINZ, MICHAEL、STEZOWSKI, JOHN J.、HARVEY, RONALD G.

  DOI：——

  日期：——