3'-O-acetyl-4'-thiothymidine | 175470-97-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3'-O-acetyl-4'-thiothymidine
• 英文别名: 1-(3-O-acetyl-2-deoxy-4-thio-β-D-ribofuranosyl)thymine；[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)thiolan-3-yl] acetate
• CAS: 175470-97-0
• 化学式: C₁₂H₁₆N₂O₅S
• 分子量: 300.335
• InChiKey: ZTTIKRCYUBAUHJ-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-O-acetyl-4'-thiothymidine 在 吡啶 、 2-chloro-4H-1,2,3-dioxaphosphorin-4-one 、 三正丁胺 、 三丁基焦磷酸铵 、 碘 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 0.42h， 生成
  参考文献：
  名称：

  Amplification of 4‘-ThioDNA in the Presence of 4‘-Thio-dTTP and 4‘-Thio-dCTP, and 4‘-ThioDNA-Directed Transcription in Vitro and in Mammalian Cells

  摘要：

  Herein we describe the synthesis of 4'-thio-dTTP (1) and 4'-thio-dCTP (2) and their susceptibility for PCR amplification. Double stranded 4'-thioDNAs were amplified sufficiently by KOD dash DNA polymerase under appropriate conditions. Through this PCR study, it was shown that not only DNA-directed 4'-thioDNA synthesis but also 4'-thioDNA-directed 4'-thioDNA synthesis occurred in the presence of 1 and/or 2. We then tested the ability of the resulting 4'-thioDNAs to act as templates for transcription. In this experiment, the 4'-thioDNAs as templates afforded RNA in 38-49% yield relative to the case of the natural DNA template. We further investigated whether transcription occurred in mammalian cells. As a result, not only natural DNA but also 4'-thioDNAs were transcribed to afford a shRNA which showed gene-silencing effects via RNAi machinery.

  DOI：

  10.1021/ja075953c
• 作为产物：
  描述：

  1-(3-O-acetyl-2-deoxy-5-O-dimethoxytrityl-4-thio-β-D-ribofuranosyl)thymine 在 溶剂黄146 作用下， 以 水 为溶剂， 生成 3'-O-acetyl-4'-thiothymidine
  参考文献：
  名称：

  Compounds and oligomeric compounds comprising novel nucleobases

  摘要：

  本发明涉及包含新型核碱基的核苷酸组合物以及包含至少一种此类核苷酸的寡聚合物化合物。这些寡聚合物化合物通常具有比没有这种修饰的寡聚合物化合物更强的结合亲和性能。这些寡聚合物化合物可用于调查和治疗等用途。

  公开号：

  US20040033973A1

文献信息

• Some Reactions of 4′-Thionucleosides and Their Sulfones
  作者：E. Louise Hancox、Richard T. Walker

  DOI：10.1080/07328319608002376

  日期：1996.1

  We report interesting and novel reactions of 4'-thionucleosides and their sulfone derivatives when a good leaving group is present in the 5'-position. The results have important implications for the phosphorylation of these nucleoside analogues by standard chemical procedures. Possible mechanisms for these reactions are discussed.