1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-β-D-ribofuranose | 1575814-80-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-β-D-ribofuranose
• 英文别名: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[[3-[3-(trifluoromethyl)diazirin-3-yl]phenyl]methoxy]oxolane-3,4-diol
• CAS: 1575814-80-0
• 化学式: C₁₄H₁₅F₃N₂O₅
• 分子量: 348.279
• InChiKey: MRGHIVNLYDDDAW-DDHJBXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-β-D-ribofuranose 在 吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 3-O-(tert-butyldimethylsilyl)-1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-5-O-(4,4′-dimethoxytrityl)-β-D-ribofuranose
  参考文献：
  名称：

  Diazirine-Containing RNA Photo-Cross-Linking Probes for Capturing microRNA Targets

  摘要：

  Here, we report the applicability of diazirine-containing RNA photo-cross-linking probes for the identification of microRNA (miRNA) targets. The RNA cross-linking probes were synthesized by substituting the RNA nucleobases with nucleoside analogues such as 1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)]benzyl-β-d-ribofuranose or 1-O-[4-(3-trifluoromethyl-3H-diazirin-3-yl)]benzyl-β-D-ribofuranose that carry aryl trifluoromethyl diazirine moieties. The probes were successfully cross-linked with synthetic RNAs containing the four natural nucleosides on the opposite site of the nucleoside analogues. Furthermore, it was found that miRNAs containing these analogues were effective in regulating the expression of their target genes. Thus, RNAs containing the nucleoside analogues are promising candidates as photo-cross-linking probes to identify the target mRNAs of miRNAs.

  DOI：

  10.1021/jo402738t
• 作为产物：
  描述：

  3-碘苯甲醇 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 正丁基锂 、 三氟甲磺酸三甲基硅酯 、 盐酸羟胺 、 四丁基氟化铵 、 氨 、 碘 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 57.0h， 生成 1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)benzyl]-β-D-ribofuranose
  参考文献：
  名称：

  Diazirine-Containing RNA Photo-Cross-Linking Probes for Capturing microRNA Targets

  摘要：

  Here, we report the applicability of diazirine-containing RNA photo-cross-linking probes for the identification of microRNA (miRNA) targets. The RNA cross-linking probes were synthesized by substituting the RNA nucleobases with nucleoside analogues such as 1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)]benzyl-β-d-ribofuranose or 1-O-[4-(3-trifluoromethyl-3H-diazirin-3-yl)]benzyl-β-D-ribofuranose that carry aryl trifluoromethyl diazirine moieties. The probes were successfully cross-linked with synthetic RNAs containing the four natural nucleosides on the opposite site of the nucleoside analogues. Furthermore, it was found that miRNAs containing these analogues were effective in regulating the expression of their target genes. Thus, RNAs containing the nucleoside analogues are promising candidates as photo-cross-linking probes to identify the target mRNAs of miRNAs.

  DOI：

  10.1021/jo402738t

文献信息

• Diazirine-Containing RNA Photo-Cross-Linking Probes for Capturing microRNA Targets
  作者：Kosuke Nakamoto、Yoshihito Ueno

  DOI：10.1021/jo402738t

  日期：2014.3.21

  Here, we report the applicability of diazirine-containing RNA photo-cross-linking probes for the identification of microRNA (miRNA) targets. The RNA cross-linking probes were synthesized by substituting the RNA nucleobases with nucleoside analogues such as 1-O-[3-(3-trifluoromethyl-3H-diazirin-3-yl)]benzyl-β-d-ribofuranose or 1-O-[4-(3-trifluoromethyl-3H-diazirin-3-yl)]benzyl-β-D-ribofuranose that carry aryl trifluoromethyl diazirine moieties. The probes were successfully cross-linked with synthetic RNAs containing the four natural nucleosides on the opposite site of the nucleoside analogues. Furthermore, it was found that miRNAs containing these analogues were effective in regulating the expression of their target genes. Thus, RNAs containing the nucleoside analogues are promising candidates as photo-cross-linking probes to identify the target mRNAs of miRNAs.