N²-isobutyryl-8-methyl-2'-deoxyguanosine | 166184-10-7

• 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: N²-isobutyryl-8-methyl-2'-deoxyguanosine
• 英文别名: N-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-methyl-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• CAS: 166184-10-7
• 化学式: C₁₅H₂₁N₅O₅
• 分子量: 351.362
• InChiKey: RYIHOAVGTXKQPM-IVZWLZJFSA-N

物化性质

• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N²-isobutyryl-8-methyl-2'-deoxyguanosine 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-N²-isobutyryl-8-methyl-2'-deoxyguanosine
  参考文献：
  名称：

  Synthesis, Miscoding Specificity, and Thermodynamic Stability of Oligodeoxynucleotide Containing 8-Methyl-2‘-deoxyguanosine

  摘要：

  8-Methyl-2'-deoxyguanosine (8-MedG) was synthesized by reacting dG under the methyl radical generating system and incorporated into oligodeoxynucleotides using phosphoramidite techniques. The site-specifically modified oligodeoxynucleotide containing a single 8-MedG was then used as a template for primer extension reactions catalyzed by the 3'-5' exonuclease-free (exo(-)) Klenow fragment of Escherichia coli DNA polymerase I and mammalian DNA polymerase alpha. Primer extension catalyzed by the exo(-) Klenow fragment, readily passed the 8-MedG lesion in the template while that catalyzed by pol alpha was retarded opposite the lesion. The fully extended products formed during DNA synthesis were analyzed to quantify the miscoding specificities of 8-MedG;. Both DNA polymerases incorporated primarily dCMP, the correct base opposite the lesion, along with small amounts of incorporation of dAMP and dAMP. In addition, two-base deletion was observed only when the exo(-) Klenow fragment was used. The thermodynamic stability of 8-MedG in the duplex was also studied. The duplex containing 8-MedG:dG was more thermally and thermodynamically stable than that of dG:dG. The duplex containing 8-MedG:dA was more thermodynamically stable than that of dG:dA. We conclude that 8-MedG is a miscoding lesion and capable of generating G --> C and G --> T transversions and deletion in cells.

  DOI：

  10.1021/tx9601059
• 作为产物：
  描述：

  异丁酸酐 、 8-methyl-2'-deoxyguanosine 在 吡啶 、 ammonium hydroxide 、 三甲基氯硅烷 作用下， 生成 N²-isobutyryl-8-methyl-2'-deoxyguanosine
  参考文献：
  名称：

  Structure-Activity Study of Oligodeoxynucleotides Which Inhibit Thrombin

  摘要：

  The 15-mer oligodeoxynucleotide GGTTGGTGTGGTTGG is a potent inhibitor of thrombin and it forms a stable, highly compact structure in solution. Deletions and substitutions by abasic residues, 2'-deoxyinosine, 7-deaza-2'-deoxyguanosine and 8-methyl-2'-deoxyguanosine show that the structural features of the oligodeoxynucleotide are important for its biological activity.

  DOI：

  10.1080/15257779508012546