9-N-[(5'-O-(4,4'-dimethoxytrityl)-2'-O-(tetrahydrofuranyl)-β-D-ribo-pentafuranosyl)methyl]-N6-benzoyladenine | 726186-39-6

• 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: 9-N-[(5'-O-(4,4'-dimethoxytrityl)-2'-O-(tetrahydrofuranyl)-β-D-ribo-pentafuranosyl)methyl]-N6-benzoyladenine
• 英文别名: 9-N-[(5'-O-(4,4'-dimethoxytrityl)-2'-O-(tetrahydrofuranyl)-β-D-ribo-pentafuranosyl)methyl]-N⁶-benzoyladenine
• CAS: 726186-39-6
• 化学式: C₄₃H₄₃N₅O₈
• 分子量: 757.843
• InChiKey: PWZPILGCVUUQOM-BBTOVIHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  56.0
• 可旋转键数：
  14.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  148.31
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  吡啶 、 1-[(2-氯苯氧基)-(1,2,4-三唑-1-基)磷酰基]-1,2,4-三唑 、 9-N-[(5'-O-(4,4'-dimethoxytrityl)-2'-O-(tetrahydrofuranyl)-β-D-ribo-pentafuranosyl)methyl]-N6-benzoyladenine 在 N-甲基咪唑 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Homo-N-oligonucleotides (N1/N9−C1‘ Methylene Bridge Oligonucleotides):  Nucleic Acids with Left-Handed Helicity

  摘要：

  Oligonucleotides containing a methylene bridge between N1 or N9 of the heterocyclic base and C1' of the pentofuranosyl ring (homo-N-oligonucleotides) were synthesized. Melting curves revealed that such homo-type oligomers could cross-pair with complementary homo-type or natural oligomers. Circular-dichroic studies provide evidence that the homo-type dinners have a left-handed stacked conformation and further suggest that single-stranded and double-stranded homo-type oligomers adopt a left-handed conformation, while duplexes with natural oligomers or nucleic acids form RNA-like right-handed helices. NMR spectroscopy (NOESY) provides supporting evidence for a left-handed stacked conformation of the homo-type dimer, while atomic force microscopy indicates a left-handed helical conformation of homotype dsDNA. Homo-type dinners and oligomers showed high resistance to digestion by snake-venom and calf-spleen phosphodiesterases and nuclease S1.

  DOI：

  10.1021/ja049865t
• 作为产物：
  描述：

  N-{9-[(2S,3S,3aR,9aR)-5,5,7,7-Tetraisopropyl-3-(tetrahydro-furan-2-yloxy)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-ylmethyl]-9H-purin-6-yl}-benzamide 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 9-N-[(5'-O-(4,4'-dimethoxytrityl)-2'-O-(tetrahydrofuranyl)-β-D-ribo-pentafuranosyl)methyl]-N6-benzoyladenine
  参考文献：
  名称：

  Homo-N-oligonucleotides (N1/N9−C1‘ Methylene Bridge Oligonucleotides):  Nucleic Acids with Left-Handed Helicity

  摘要：

  Oligonucleotides containing a methylene bridge between N1 or N9 of the heterocyclic base and C1' of the pentofuranosyl ring (homo-N-oligonucleotides) were synthesized. Melting curves revealed that such homo-type oligomers could cross-pair with complementary homo-type or natural oligomers. Circular-dichroic studies provide evidence that the homo-type dinners have a left-handed stacked conformation and further suggest that single-stranded and double-stranded homo-type oligomers adopt a left-handed conformation, while duplexes with natural oligomers or nucleic acids form RNA-like right-handed helices. NMR spectroscopy (NOESY) provides supporting evidence for a left-handed stacked conformation of the homo-type dimer, while atomic force microscopy indicates a left-handed helical conformation of homotype dsDNA. Homo-type dinners and oligomers showed high resistance to digestion by snake-venom and calf-spleen phosphodiesterases and nuclease S1.

  DOI：

  10.1021/ja049865t