S4-(2-氰基乙基)-4-硫代胸腺嘧啶脱氧核苷 | 869355-26-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: S4-(2-氰基乙基)-4-硫代胸腺嘧啶脱氧核苷
• 英文名称: S4-(2-Cyanoethyl)-4-thiothymidine
• 英文别名: 3-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-2-oxopyrimidin-4-yl]sulfanylpropanenitrile
• CAS: 869355-26-0
• 化学式: C₁₃H₁₇N₃O₄S
• 分子量: 311.362
• InChiKey: NNFUOOPYEYBTCR-HBNTYKKESA-N

物化性质

• 沸点：
  579.0±60.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S4-(2-氰基乙基)-4-硫代胸腺嘧啶脱氧核苷 在 吡啶 、 四氮唑 、 二异丙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 C₄₃H₅₂N₅O₇PS
  参考文献：
  名称：

  Remarkable stabilization of antiparallel DNA triplexes by strong stacking effects of consecutively modified nucleobases containing thiocarbonyl groups

  摘要：

  The consecutive arrangement of 2'-deoxy-6-thioguanosines (s(6)Gs) and 4-thiothymidines (s(4)Ts) in antiparallel triplex-forming oligonucleotides (TFOs) considerably stabilized the resulting antiparallel triplexes with high base recognition ability by the strong stacking effects of thiocarbonyl groups. This result was remarkable because chemical modifications of the sugar moieties and nucleobases of antiparallel TFOs generally destabilize triplex structures. Moreover, in comparison with unmodified TFOs, it was found that TFOs containing s(6)Gs and s(4)Ts could selectively bind to the complementary DNA duplex but not to mismatched DNA duplexes or single-stranded RNA. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.079
• 作为产物：
  描述：

  C₂₅H₄₅N₃O₄SSi₂ 在 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以65%的产率得到S4-(2-氰基乙基)-4-硫代胸腺嘧啶脱氧核苷
  参考文献：
  名称：

  Remarkable stabilization of antiparallel DNA triplexes by strong stacking effects of consecutively modified nucleobases containing thiocarbonyl groups

  摘要：

  The consecutive arrangement of 2'-deoxy-6-thioguanosines (s(6)Gs) and 4-thiothymidines (s(4)Ts) in antiparallel triplex-forming oligonucleotides (TFOs) considerably stabilized the resulting antiparallel triplexes with high base recognition ability by the strong stacking effects of thiocarbonyl groups. This result was remarkable because chemical modifications of the sugar moieties and nucleobases of antiparallel TFOs generally destabilize triplex structures. Moreover, in comparison with unmodified TFOs, it was found that TFOs containing s(6)Gs and s(4)Ts could selectively bind to the complementary DNA duplex but not to mismatched DNA duplexes or single-stranded RNA. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.079