5-(5’-O-dimethoxytrityl-2’-deoxy-D-ribofuranosyl)-6-methyl-2-phenoxyacetylaminopyridine | 1449482-13-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-(5’-O-dimethoxytrityl-2’-deoxy-D-ribofuranosyl)-6-methyl-2-phenoxyacetylaminopyridine
• CAS: 1449482-13-6
• 化学式: C₄₀H₄₀N₂O₇
• 分子量: 660.767
• InChiKey: WWQJDQKBEUXJNL-HKIDPNTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.62
• 重原子数：
  49.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  108.37
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-(5’-O-dimethoxytrityl-2’-deoxy-D-ribofuranosyl)-6-methyl-2-phenoxyacetylaminopyridine 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以83%的产率得到5-{5’-O-dimethoxytrityl-3’-O-2-cyanoethoxy(diisopropylamino)phosphino-2’-deoxy-D-ribofuranosyl}-6-methyl-2-phenoxyacetylaminopyridine
  参考文献：
  名称：

  A 2-AMINO-6-METHYLPYRIDIN-5-YL NUCLEOBASE FOR GC BASE PAIR RECOGNITION IN THE PARALLEL TRIPLEX DNA

  摘要：

  DNA triple helices containing consecutive C+H center dot GC triplets are unstable at neutral pH because protonations of cytosines into the third strand are necessary. Previously, a 2-aminopyridin-5-yl nucleobase (P) was developed and has been widely used as a substitute for the cytosine nucleobase. In this work, we designed a 2-amino-6-methylpyridin-5-yl nucleobase (P-Me), which could preferentially adopt an anti-orientation by the 6-methyl group. This might lead to formation of a stable base triplet with a GC base pair compared to P. We also synthesized 15-mer triplex-forming oligonucleotides (TFOs) containing P-Me by the standard solid-phase method and evaluated the triplex stability of the TFOs at neutral pH by UV melting experiments.

  DOI：

  10.3987/com-12-s(n)68
• 作为产物：
  描述：

  2-amino-5-[3’,5’-di-O-tert-butyldimethylsilyl-(2’-deoxy-D-ribofuranosyl)]-6-methylpyridine 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 生成 5-(5’-O-dimethoxytrityl-2’-deoxy-D-ribofuranosyl)-6-methyl-2-phenoxyacetylaminopyridine
  参考文献：
  名称：

  A 2-AMINO-6-METHYLPYRIDIN-5-YL NUCLEOBASE FOR GC BASE PAIR RECOGNITION IN THE PARALLEL TRIPLEX DNA

  摘要：

  DNA triple helices containing consecutive C+H center dot GC triplets are unstable at neutral pH because protonations of cytosines into the third strand are necessary. Previously, a 2-aminopyridin-5-yl nucleobase (P) was developed and has been widely used as a substitute for the cytosine nucleobase. In this work, we designed a 2-amino-6-methylpyridin-5-yl nucleobase (P-Me), which could preferentially adopt an anti-orientation by the 6-methyl group. This might lead to formation of a stable base triplet with a GC base pair compared to P. We also synthesized 15-mer triplex-forming oligonucleotides (TFOs) containing P-Me by the standard solid-phase method and evaluated the triplex stability of the TFOs at neutral pH by UV melting experiments.

  DOI：

  10.3987/com-12-s(n)68