3',5'-di-O-trifluoroacetyl-5-iodo-2'-deoxyuridine | 149798-19-6

• 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: 3',5'-di-O-trifluoroacetyl-5-iodo-2'-deoxyuridine
• 英文别名: [(2R,3S,5R)-5-(5-iodo-2,4-dioxopyrimidin-1-yl)-3-(2,2,2-trifluoroacetyl)oxyoxolan-2-yl]methyl 2,2,2-trifluoroacetate
• CAS: 149798-19-6
• 化学式: C₁₃H₉F₆IN₂O₇
• 分子量: 546.119
• InChiKey: YVWQXPDLPIPGGS-RRKCRQDMSA-N

物化性质

• 密度：
  2.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-trifluoroacetyl-5-iodo-2'-deoxyuridine 在 四(三苯基膦)钯 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-乙炔-2-脱氧尿苷
  参考文献：
  名称：

  Ru(II) 和 Os(II) 核苷和寡核苷酸：合成和性质

  摘要：

  报道了使用固相亚磷酰胺化学将聚吡啶 Ru(II) 和 Os(II) 复合物定点掺入 DNA 寡核苷酸的通用和通用方法。含有 [(bpy)(2)M(3-ethynyl-1,10-phenanthroline)](2+) (M = Ru, Os) 金属中心共价连接到 2'-脱氧尿苷的 5 位的新型核苷是合成，并研究了它们的电化学和光物理性质。Ru(II) 核苷在磷酸盐缓冲液 pH 7.0（tau = 1.08 微米）中表现出相当长的激发态，与相对较高的发射量子效率（phi = 0.051）相关。吸收和发射光谱的溶剂依赖性与发射 MLCT 状态一致，其中电荷定位发生在扩展的杂环连接的菲咯啉上。相比之下，含 Os(II) 的核苷在水性环境中非常不发射（tau = 0.027 micros，phi = 1 x 10(-4)）。含金属的核苷被转化为其亚磷酰胺，并用于高产率的修饰寡核苷酸制备。通过吸收和

  DOI：

  10.1021/ja0123103
• 作为产物：
  描述：

  碘苷 在 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 生成 3',5'-di-O-trifluoroacetyl-5-iodo-2'-deoxyuridine
  参考文献：
  名称：

  Antisense oligonucleotides comprising 5-aminoalkyl pyrimidine nucleotides

  摘要：

  将天然核苷酸替换为带有阳离子基团的非天然带电核苷酸（或其类似物）会导致寡脱氧核苷酸带有减少的电荷，但在低离子强度下与DNA结合的能力不减。我们现在发现，通过向碱基引入带有连接的阳离子基团，可以使DNA完全成为带电核酸，而不影响双链形成。由此产生的寡核苷酸具有耐核酸酶的额外优势。

  公开号：

  US05596091A1

文献信息

• Aminooxy functionalized oligomers
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US06576752B1

  公开（公告）日：2003-06-10

  The present invention provides oligomers which are specifically hybridizable with a selected sequence of RNA or DNA wherein at least one of the nucleoside moieties of the oligomer is modified to include an aminooxy linkage. These oligomers are useful for diagnostic, therapeutic and investigative purposes.

  本发明提供了可以与所选的RNA或DNA序列特异性杂交的寡聚物，其中寡聚物的核苷酸基团中至少有一个被修改以包括氨氧链。这些寡聚物可用于诊断、治疗和研究目的。
• Guanidinium functionalized oligonucleotides and method/synthesis
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US06534639B1

  公开（公告）日：2003-03-18

  The present invention provides oligomers which are specifically hybridizable with a selected sequence of RNA or DNA wherein at least one of the nucleoside moieties of the oligomer is modified to include a guanidinium group. These oligomers are useful for diagnostic, therapeutic and investigative purposes.

  本发明提供了寡聚物，其能够特异性地与所选的RNA或DNA序列杂交，其中至少一种核苷酸基团被修饰以包括一种鸟氨酸基团。这些寡聚物可用于诊断、治疗和研究目的。
• Guanidinium functionalized oligomers and methods
  申请人：——

  公开号：US20030092046A1

  公开（公告）日：2003-05-15

  The present invention provides oligomers which are specifically hybridizable with a selected sequence of RNA or DNA wherein at least one of the nucleoside moieties of the oligomer is modified to include a guanidinium group. These oligomers are useful for diagnostic, therapeutic and investigative purposes.

  本发明提供了寡核苷酸，它们与RNA或DNA的选定序列具有特异性杂交性，其中至少一个核苷酸基团被修饰以包括一种鸟氨酸基团。这些寡核苷酸对于诊断、治疗和调查目的非常有用。
• Aminooxy functionalized oligomers, oligomer arrays and methods of using them
  申请人：——

  公开号：US20030113769A1

  公开（公告）日：2003-06-19

  The present invention provides oligomers which are specifically hybridizable with a selected sequence of RNA or DNA wherein at least one of the nucleoside moieties of the oligomer is modified to include an aminooxy linkage. These oligomers are useful for diagnostic, therapeutic and investigative purposes.

  本发明提供了能够与所选的RNA或DNA序列特异性杂交的寡聚物，其中寡聚物的核苷酸基团中至少一个被修饰为含有氨氧基连接。这些寡聚物可用于诊断、治疗和研究目的。
• Zwitterionic DNA
  作者：Hiromasa Hashimoto、Marek G. Nelson、Christopher Switzer

  DOI：10.1021/ja00069a009

  日期：1993.8

  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.