9-N-[(2',3'-O-diacetyl-β-D-ribo-pentofuranosyl)methyl]-N⁶-benzoyladenine | 726186-32-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-N-[(2',3'-O-diacetyl-β-D-ribo-pentofuranosyl)methyl]-N⁶-benzoyladenine
• CAS: 726186-32-9
• 化学式: C₂₂H₂₃N₅O₇
• 分子量: 469.454
• InChiKey: BQXAZDLVVLVQSL-OGWHTMIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  154.76
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  9-N-[(2',3'-O-diacetyl-β-D-ribo-pentofuranosyl)methyl]-N⁶-benzoyladenine 在 吡啶 、 ammonium hydroxide 、 苯甲基-2-磺酰三硝基三氮唑 作用下， 反应 49.0h， 生成 Phosphoric acid (2R,3S,4S,5S)-5-(6-amino-purin-9-ylmethyl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-3-yl ester (2R,3S,4R,5S)-5-(6-amino-purin-9-ylmethyl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester
  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：

  9-N-[(β-D-ribo-pentafuranosyl)methyl]-N⁶-benzoyladenine 在 吡啶 、 溶剂黄146 作用下， 反应 4.0h， 生成 9-N-[(2',3'-O-diacetyl-β-D-ribo-pentofuranosyl)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