N-(deoxyguanosin-8-yl)-4'-fluoro-4-aminobiphenyl

• 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: N-(deoxyguanosin-8-yl)-4'-fluoro-4-aminobiphenyl
• 英文别名: N-(deoxyguanosin-8-yl)-4'-fluoro-4-aminobi-phenyl；2-amino-8-[4-(4-fluorophenyl)anilino]-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• 化学式: C₂₂H₂₁FN₆O₄
• 分子量: 452.445
• InChiKey: FARSOMVJYOVVHG-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  147
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2'-脱氧鸟苷 、 [4-(4-fluorophenyl)-N-(2,2,2-trifluoroacetyl)anilino] acetate 在 citrate buffer 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 N-(deoxyguanosin-8-yl)-4'-fluoro-4-aminobiphenyl
  参考文献：
  名称：

  Conformational Heterogeneity of Arylamine-Modified DNA:  ¹⁹F NMR Evidence

  摘要：

  One- and two-dimensional F-19 NMR spectroscopy was used to investigate the conformational heterogeneity of two arylamine-modified DNA duplexes, d[CTTCTTG*ACCTC]. d[GAGGTCAAGAAG], in which G* is either N-(deoxyguanosin-8-yl)-4'-fluoro-4-aminobiphenyl (dG-C8-FABP) (I) or N-(deoxyguanosin-8-yl)-7-fluoro-2-aminofluorene (dG-C8-FAF (II). The F-19 NMR spectrum of I showed a single peak, while that of II revealed two prominent signals with a 55:45 ratio, in good agreement with previous H-1 NMR results (Cho et al. Biochemistry 1992, 31, 9587-9602; 1994, 33, 1373-1384). Slow interconversion between the two conformations of II was established by temperature-dependent two-dimensional F-19 NMR chemical exchange spectre. On the basis of magnetic anisotropy effects and isotopic solvent-induced shifts, the F-19 signals at -117.31 and -118.09 ppm in the F-19 NMR spectrum of II were assigned to a relatively undisturbed ''B-type'' conformer and a highly perturbed ''stacked'' conformer, respectively. Analysis of the temperature dependent (5-40 degrees C) line shapes by computer simulation yielded an interconversion barrier (Delta G(double dagger) of 14.0 kcal/mol with a chemical exchange time of 2 ms at 30 degrees C. This new F-19 approach should be very useful in investigating the sequence-dependent conformational heterogeneity of arylamine-modified DNA.

  DOI：

  10.1021/ja9632771

文献信息

• Conformational Heterogeneity of Arylamine-Modified DNA:  ¹⁹F NMR Evidence
  作者：Li Zhou、Masoumeh Rajabzadeh、Daniel D. Traficante、Bongsup P. Cho

  DOI：10.1021/ja9632771

  日期：1997.6.1

  One- and two-dimensional F-19 NMR spectroscopy was used to investigate the conformational heterogeneity of two arylamine-modified DNA duplexes, d[CTTCTTG*ACCTC]. d[GAGGTCAAGAAG], in which G* is either N-(deoxyguanosin-8-yl)-4'-fluoro-4-aminobiphenyl (dG-C8-FABP) (I) or N-(deoxyguanosin-8-yl)-7-fluoro-2-aminofluorene (dG-C8-FAF (II). The F-19 NMR spectrum of I showed a single peak, while that of II revealed two prominent signals with a 55:45 ratio, in good agreement with previous H-1 NMR results (Cho et al. Biochemistry 1992, 31, 9587-9602; 1994, 33, 1373-1384). Slow interconversion between the two conformations of II was established by temperature-dependent two-dimensional F-19 NMR chemical exchange spectre. On the basis of magnetic anisotropy effects and isotopic solvent-induced shifts, the F-19 signals at -117.31 and -118.09 ppm in the F-19 NMR spectrum of II were assigned to a relatively undisturbed ''B-type'' conformer and a highly perturbed ''stacked'' conformer, respectively. Analysis of the temperature dependent (5-40 degrees C) line shapes by computer simulation yielded an interconversion barrier (Delta G(double dagger) of 14.0 kcal/mol with a chemical exchange time of 2 ms at 30 degrees C. This new F-19 approach should be very useful in investigating the sequence-dependent conformational heterogeneity of arylamine-modified DNA.