3'-O-Acetyl-5'-oxothymidine | 202722-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3'-O-Acetyl-5'-oxothymidine
• 英文别名: 3'-O-acetylthymidine-5'-aldehyde；(2S,3S,5R)-3-acetyloxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolane-2-carboxylic acid
• CAS: 202722-92-7
• 化学式: C₁₂H₁₄N₂O₇
• 分子量: 298.252
• InChiKey: BRPPKNWURHYORJ-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3'-O-Acetyl-5'-oxothymidine 在 二苯基磷酸 、 氨 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Oligodeoxynucleotides containing amide-linked LNA-type dinucleotides: synthesis and high-affinity nucleic acid hybridization

  摘要：

  该研究描述了三种不同的酰胺连接 LNA 型二核苷酸的合成及其与 9 聚体和 17 聚体寡脱氧核苷酸的结合；与参考 DNA-RNA 双链相比，三种二聚体之一（5′-DNA*LNA 二聚体）的结合显著提高了双链的热稳定性。

  DOI：

  10.1039/b111000d
• 作为产物：
  描述：

  3'-O-Acetyl-5'-O-tert-butyl-5'-oxothymidine 在 三氟乙酸 作用下， 反应 4.0h， 生成 3'-O-Acetyl-5'-oxothymidine
  参考文献：
  名称：

  Butterfield, Katharine; Thomas, Eric J., Journal of the Chemical Society. Perkin transactions I, 1998, # 4, p. 737 - 745

  摘要：

  DOI：

文献信息

• Synthesis and biological evaluation of novel neamine–nucleoside conjugates potentially targeting to RNAs
  作者：Yanli Xu、Hongwei Jin、Zhenjun Yang、Liangren Zhang、Lihe Zhang

  DOI：10.1016/j.tet.2009.04.084

  日期：2009.7

  Eighteen novel neamine-nucleoside conjugates with ethylenediamine-lysine or ethylenediamine-arginine as the linker were synthesized and their potential binding to A site of 16S RNA and TAR RNA was evaluated using SPR (surface plasmon resonance). Compared with neamine, compounds 10i and 10q show 6.3 and 4.8 times potential in binding to A site of 16S RNA and eight and six times potential in binding to TAR RNA, respectively. According to the data of SPR, it indicates that amino acid residue and nucleobase moieties of the designed neamine-nucleosides conjugates exhibit the important contributions for the binding to A site of 16S RNA and TAR RNA. The molecular docking Study on the interaction between the ligands and A site of 16S RNA is in agreement with the experimental data. The novel type of modification may provide a promising way for the development of neamine derivatives effectively targeting to RNAs. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of aminodisaccharide–nucleoside conjugates for RNA binding
  作者：Li Cai、Qin Li、Bo Ren、Zhen-Jun Yang、Liang-Ren Zhang、Li-He Zhang

  DOI：10.1016/j.tet.2007.06.002

  日期：2007.8

  Two types of aminodisaccharide-nucleoside conjugates were synthesized by the condensation of azidodisaccharide and nucleoside using aliphatic diamine as a linker. The corresponding azidodisaccharides could be yielded from neamine in good yield. The binding properties to 16S RNA of these conjugates were evaluated by SPR. It was found that the nucleobase played a significant role in the binding of these conjugates to 16S RNA and a shorter linker between the aminodisaccharide and nucleoside was favorable for 16S RNA binding. (c) 2007 Elsevier Ltd. All rights reserved.