[(2S,5R)-5-[2,4-dioxo-5-[(E)-2-[4-[3-(trifluoromethyl)diazirin-3-yl]phenyl]ethenyl]pyrimidin-1-yl]oxolan-2-yl]methyl dihydrogen phosphate | 161860-50-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: [(2S,5R)-5-[2,4-dioxo-5-[(E)-2-[4-[3-(trifluoromethyl)diazirin-3-yl]phenyl]ethenyl]pyrimidin-1-yl]oxolan-2-yl]methyl dihydrogen phosphate
• CAS: 161860-50-0
• 化学式: C₁₉H₁₈F₃N₄O₇P
• 分子量: 502.343
• InChiKey: UMTTWDRJXCDSIA-DIGGSNQISA-N

物化性质

• 密度：
  1.74±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  155.57
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [(2S,5R)-5-[2,4-dioxo-5-[(E)-2-[4-[3-(trifluoromethyl)diazirin-3-yl]phenyl]ethenyl]pyrimidin-1-yl]oxolan-2-yl]methyl dihydrogen phosphate 生成 2',3'-dideoxy-E-5-{4-[3-(trifluoromethyl)-3H-diazirin-3-yl]styryl}uridine 5'-diphosphate
  参考文献：
  名称：

  Synthetic Nucleoside and Nucleotides. XXXIV. Photoaffinity Labeling of HIV Reverse Transcriptase: Synthesis and Utilization of 2′,3′-Dideoxy Uridylate Analogs Bearing Aryl(trifluor0methyl)-Diazirine Moiety

  摘要：

  In order to develop a photoaffinity labeling reagent for HIV-1 reverse transcriptase, a 2',3'-dideoxyUTP analog bearing a photo-reactive group at the 5-position of the uracil ring, 2',3'-dideoxy-E-5-[4-[3-(trifluoromethyl)-3H-diazirin-3-yl]styryl]-UTP, was designed and synthesized. This photo-reactive analog could preferentially bind to the 66 kDa subunit of the p66/p51 heterodimeric HIV-1 reverse transcriptase under irradiation by near-ultraviolet light (365 nm).

  DOI：

  10.1080/07328319608002409
• 作为产物：
  描述：

  3-(4-ethenylphenyl)-3-trifluoromethyl-3H-diazirine 在 磷酸三乙酯 、 三氯氧磷 作用下， 反应 24.0h， 生成 [(2S,5R)-5-[2,4-dioxo-5-[(E)-2-[4-[3-(trifluoromethyl)diazirin-3-yl]phenyl]ethenyl]pyrimidin-1-yl]oxolan-2-yl]methyl dihydrogen phosphate
  参考文献：
  名称：

  Synthetic Nucleoside and Nucleotides. XXXIV. Photoaffinity Labeling of HIV Reverse Transcriptase: Synthesis and Utilization of 2′,3′-Dideoxy Uridylate Analogs Bearing Aryl(trifluor0methyl)-Diazirine Moiety

  摘要：

  In order to develop a photoaffinity labeling reagent for HIV-1 reverse transcriptase, a 2',3'-dideoxyUTP analog bearing a photo-reactive group at the 5-position of the uracil ring, 2',3'-dideoxy-E-5-[4-[3-(trifluoromethyl)-3H-diazirin-3-yl]styryl]-UTP, was designed and synthesized. This photo-reactive analog could preferentially bind to the 66 kDa subunit of the p66/p51 heterodimeric HIV-1 reverse transcriptase under irradiation by near-ultraviolet light (365 nm).

  DOI：

  10.1080/07328319608002409