4-N-benzoyl-5-(6-N-(trifluoroacetyl)aminohexyl)-2'-deoxycytidine | 149798-25-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 4-N-benzoyl-5-(6-N-(trifluoroacetyl)aminohexyl)-2'-deoxycytidine
• 英文别名: 4-N-benzoyl-5-[6-N-(trifluoroacetyl)aminohexyl]-2'-deoxycytidine
• CAS: 149798-25-4
• 化学式: C₂₄H₂₉F₃N₄O₆
• 分子量: 526.513
• InChiKey: LHKMBBRBYDIOAA-IPMKNSEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  142.78
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-N-benzoyl-5-(6-N-(trifluoroacetyl)aminohexyl)-2'-deoxycytidine 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 5-(6-N-(trifluoroacetyl)aminohexyl)-4-N-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine 2-cyanoethyl N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  Zwitterionic DNA

  摘要：

  As a strategy to make DNA net charge neutral, oligodeoxynucleotides bearing pyrimidine 5-omega-aminohexyl substituents have been synthesized and characterized. The resultant zwitterionic oligomers bind to natural DNA at low ionic strength as well or better than does natural DNA with itself, even when all of the nucleotides in a given single. strand are rendered zwitterionic. As would be expected, stabilities of duplexes bearing zwitterionic strands are relatively insensitive to changes in solution ionic strength as compared with natural DNA. Somewhat surprising, however, is the finding that a DNA duplex composed of a fully zwitterionic strand and a natural complementary strand exhibits no change in stability over a 20-fold change in ionic strength. Thus, double- and single-stranded states in this case have equivalent charge densities, consistent with the zwitterionic strand contributing no net charge. Stabilization due to the ammonium ions was verified by comparing free energies of DNA duplexes bearing hexyl tethered ammonium ions with those bearing simply hexyl groups devoid of ammonium ions. This comparison showed that without an added positive ammonium ion, the hexyl tether itself has a severe and cumulative unfavorable effect on duplex stability. Finally, zwitterionic nucleotides are found to distinguish matched from mismatched nucleotides in complementary DNA strands to a degree that rivals natural DNA.

  DOI：

  10.1021/ja00069a009
• 作为产物：
  描述：

  5-(6-N-(trifluoroacetyl)amino-1-hexynyl)-2'-deoxycytidine 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 反应 23.0h， 生成 4-N-benzoyl-5-(6-N-(trifluoroacetyl)aminohexyl)-2'-deoxycytidine
  参考文献：
  名称：

  Zwitterionic DNA

  摘要：

  As a strategy to make DNA net charge neutral, oligodeoxynucleotides bearing pyrimidine 5-omega-aminohexyl substituents have been synthesized and characterized. The resultant zwitterionic oligomers bind to natural DNA at low ionic strength as well or better than does natural DNA with itself, even when all of the nucleotides in a given single. strand are rendered zwitterionic. As would be expected, stabilities of duplexes bearing zwitterionic strands are relatively insensitive to changes in solution ionic strength as compared with natural DNA. Somewhat surprising, however, is the finding that a DNA duplex composed of a fully zwitterionic strand and a natural complementary strand exhibits no change in stability over a 20-fold change in ionic strength. Thus, double- and single-stranded states in this case have equivalent charge densities, consistent with the zwitterionic strand contributing no net charge. Stabilization due to the ammonium ions was verified by comparing free energies of DNA duplexes bearing hexyl tethered ammonium ions with those bearing simply hexyl groups devoid of ammonium ions. This comparison showed that without an added positive ammonium ion, the hexyl tether itself has a severe and cumulative unfavorable effect on duplex stability. Finally, zwitterionic nucleotides are found to distinguish matched from mismatched nucleotides in complementary DNA strands to a degree that rivals natural DNA.

  DOI：

  10.1021/ja00069a009