2'-Deoxy-O⁶-<(p-nitrophenyl)ethyl>-N²,3',5'-triacetylguanosine | 132183-38-1

• 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: 2'-Deoxy-O⁶-<(p-nitrophenyl)ethyl>-N²,3',5'-triacetylguanosine
• 英文别名: [(2R,3S,5R)-5-[2-acetamido-6-[2-(4-nitrophenyl)ethoxy]purin-9-yl]-3-acetyloxyoxolan-2-yl]methyl acetate
• CAS: 132183-38-1
• 化学式: C₂₄H₂₆N₆O₉
• 分子量: 542.505
• InChiKey: CRPRZBKAGAVNCM-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  190
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2'-Deoxy-O⁶-<(p-nitrophenyl)ethyl>-N²,3',5'-triacetylguanosine 在 吡啶 、 亚硝酸特丁酯 、 氢氟酸 、 氨 作用下， 反应 144.0h， 生成 2-fluoro-O⁶-(2-(p-nitrophenyl)ethyl)-2'-deoxyinosine
  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：

  2'-脱氧鸟苷 在 吡啶 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.5h， 生成 2'-Deoxy-O⁶-<(p-nitrophenyl)ethyl>-N²,3',5'-triacetylguanosine
  参考文献：
  名称：

  Synthesis of Oligonucleotide Adducts of the Bay Region Diol Epoxide Metabolites of Carcinogenic Polycyclic Aromatic Hydrocarbons

  摘要：

  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.

  DOI：

  10.1021/jo00122a048

文献信息

• 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：——