5-{5’-O-dimethoxytrityl-3’-O-2-cyanoethoxy(diisopropylamino)phosphino-2’-deoxy-D-ribofuranosyl}-2-phenoxyacetylaminopyridine | 1449482-16-9

• 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-3’-O-2-cyanoethoxy(diisopropylamino)phosphino-2’-deoxy-D-ribofuranosyl}-2-phenoxyacetylaminopyridine
• 英文别名: N-[5-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]pyridin-2-yl]-2-phenoxyacetamide
• CAS: 1449482-16-9
• 化学式: C₄₈H₅₅N₄O₈P
• 分子量: 846.96
• InChiKey: KXQQAELHRCFFRQ-VNDMEWTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  61
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  5-[3’,5’-di-O-tert-butyldimethylsilyl-(2’-deoxy-D-ribofuranosyl)]-2-phenoxyacetylaminopyridine 在 吡啶 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 5-{5’-O-dimethoxytrityl-3’-O-2-cyanoethoxy(diisopropylamino)phosphino-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

文献信息

• A 2-AMINO-6-METHYLPYRIDIN-5-YL NUCLEOBASE FOR GC BASE PAIR RECOGNITION IN THE PARALLEL TRIPLEX DNA
  作者：Yoshiyuki Hari、Motoi Nakahara、Satoshi Obika

  DOI：10.3987/com-12-s(n)68

  日期：——

  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.