5-[3’,5’-di-O-tert-butyldimethylsilyl-(2’-deoxy-D-ribofuranosyl)]-2-phenoxyacetylaminopyridine | 1449482-10-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[3’,5’-di-O-tert-butyldimethylsilyl-(2’-deoxy-D-ribofuranosyl)]-2-phenoxyacetylaminopyridine
• CAS: 1449482-10-3
• 化学式: C₃₀H₄₈N₂O₅Si₂
• 分子量: 572.893
• InChiKey: HTNJRVQBIOHDRF-UODIDJSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.34
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  78.91
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-[3’,5’-di-O-tert-butyldimethylsilyl-(2’-deoxy-D-ribofuranosyl)]-2-phenoxyacetylaminopyridine 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 5-(5’-O-dimethoxytrityl-2’-deoxy-D-ribofuranosyl)-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-(2'-deoxy-β-D-ribofuranosyl)pyridine 在 吡啶 、 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 5-[3’,5’-di-O-tert-butyldimethylsilyl-(2’-deoxy-D-ribofuranosyl)]-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