5-O'-acetyl-3'-O-(2-thio-1,3,2-dithiaphospholano)thymidine | 1011725-24-8

• 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: 5-O'-acetyl-3'-O-(2-thio-1,3,2-dithiaphospholano)thymidine
• CAS: 1011725-24-8
• 化学式: C₁₄H₁₉N₂O₆PS₃
• 分子量: 438.486
• InChiKey: HDXFDIXANAIMCX-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  99.62
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5-O'-acetyl-3'-O-(2-thio-1,3,2-dithiaphospholano)thymidine 、 3-羟基丙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 0.08h， 生成
  参考文献：
  名称：

  New, stronger nucleophiles for nucleic acid-templated chemistry: Synthesis and application in fluorescence detection of cellular RNA

  摘要：

  Nucleic acid-templated chemistry is a promising strategy for imaging genetic sequences in living cells. Here we describe the synthesis of two new nucleophiles for use in templated nucleophilic displacements with DNA probes. The nucleophilic groups are phosphorodithioate and phosphorotrithioate; we report on synthetic methods for introducing these groups at the 3'-terminus of oligonucleotides. Both new nucleophiles are found to be more highly reactive than earlier phosphoromonothioates. This increased nucleophilicity is shown to result in more rapid templated reactions with electrophilic DNA probes. The new probes were demonstrated in detection of specific genetic sequences in solution, with clear signal over background being generated in as little as 20 min. The probes were also tested for imaging ribosomal RNA sequences in live Escherichia coli; useful signal was generated in 20 min to I h, approximately one quarter to one-half the time of earlier monothioate probes, and the signal-to-noise ratio was increased as well. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.051
• 作为产物：
  描述：

  5'-O-acetylthymidine 、 2-Chloro-1,3,2-dithiaphospholane 在 sulfur 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以46%的产率得到5-O'-acetyl-3'-O-(2-thio-1,3,2-dithiaphospholano)thymidine
  参考文献：
  名称：

  New, stronger nucleophiles for nucleic acid-templated chemistry: Synthesis and application in fluorescence detection of cellular RNA

  摘要：

  Nucleic acid-templated chemistry is a promising strategy for imaging genetic sequences in living cells. Here we describe the synthesis of two new nucleophiles for use in templated nucleophilic displacements with DNA probes. The nucleophilic groups are phosphorodithioate and phosphorotrithioate; we report on synthetic methods for introducing these groups at the 3'-terminus of oligonucleotides. Both new nucleophiles are found to be more highly reactive than earlier phosphoromonothioates. This increased nucleophilicity is shown to result in more rapid templated reactions with electrophilic DNA probes. The new probes were demonstrated in detection of specific genetic sequences in solution, with clear signal over background being generated in as little as 20 min. The probes were also tested for imaging ribosomal RNA sequences in live Escherichia coli; useful signal was generated in 20 min to I h, approximately one quarter to one-half the time of earlier monothioate probes, and the signal-to-noise ratio was increased as well. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.051