N-(2-hydroxyethyl)-N-[(5-propynyl-uracil-1-yl)acetyl]glycine tert-butyl ester | 700875-66-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-hydroxyethyl)-N-[(5-propynyl-uracil-1-yl)acetyl]glycine tert-butyl ester
• 英文别名: tert-butyl 2-[[2-(2,4-dioxo-5-prop-1-ynylpyrimidin-1-yl)acetyl]-(2-hydroxyethyl)amino]acetate
• CAS: 700875-66-7
• 化学式: C₁₇H₂₃N₃O₆
• 分子量: 365.386
• InChiKey: COOQADBPBGIUOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.93
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  121.7
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxyethyl)-N-[(5-propynyl-uracil-1-yl)acetyl]glycine tert-butyl ester 在 吡啶 、 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 2-[2-[bis(4-methoxyphenyl)-phenylmethoxy]ethyl-[2-(2,4-dioxo-5-prop-1-ynylpyrimidin-1-yl)acetyl]amino]acetic acid;N,N-diethylethanamine
  参考文献：
  名称：

  PNA-DNA Chimeras Containing 5-Alkynyl-pyrimidine PNA Units. Synthesis, Binding Properties, and Enzymatic Stability

  摘要：

  Three chimeric dimer synthons (oeg_t(NH)T, oeg_up(NH)T and oeg_uh(NH)T) containing thymine (t), 5-(1-propynyl)-uracil (up) and 5-(1-hexyn-1-yl)-uracil (uh) PNA units with N-(2-hydroxyethyl)glycine (oeg) backbone were synthesized in solution and incorporated into T-20 oligonucleotide analogues, using standard P-amidite chemistry. Insertion of dimer blocks led to destabilization of duplexes with dA(20) target. The smallest T-m drops were found for chimeras containing oeg_up(NH)T dimers. Incorporation of the chimeric synthons into the 3'-end of T-20 brought about growing resistance to 3'-exonucleolytic (SV PDE) cleavage in the order of oeg_t(NH)T < oeg_up(NH)T < oeg_uh(NH)T. Due to different endonuclease activities of 3'- and 5'-exonucleases applied, placing of five consecutive dimers at the 5'-terminus resulted in a relatively smaller, but also side-chain dependent, stabilization towards the hydrolysis by 5'-exonuclease (BS PDE). Neither exonucleases (SV and BS PDE) nor an endonuclease (Nuclease P-1) could hydrolyse the unnatural phosphodiester bond linking the 3'-OH of thymidine to the terminal OH of N-(2-hydroxyethyl)glycine PNA backbone.

  DOI：

  10.1081/ncn-120025243
• 作为产物：
  描述：

  5-(1-丙炔)-2,4(1H,3h)-嘧啶二酮 在 sodium hydroxide 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 N-(2-hydroxyethyl)-N-[(5-propynyl-uracil-1-yl)acetyl]glycine tert-butyl ester
  参考文献：
  名称：

  PNA-DNA Chimeras Containing 5-Alkynyl-pyrimidine PNA Units. Synthesis, Binding Properties, and Enzymatic Stability

  摘要：

  Three chimeric dimer synthons (oeg_t(NH)T, oeg_up(NH)T and oeg_uh(NH)T) containing thymine (t), 5-(1-propynyl)-uracil (up) and 5-(1-hexyn-1-yl)-uracil (uh) PNA units with N-(2-hydroxyethyl)glycine (oeg) backbone were synthesized in solution and incorporated into T-20 oligonucleotide analogues, using standard P-amidite chemistry. Insertion of dimer blocks led to destabilization of duplexes with dA(20) target. The smallest T-m drops were found for chimeras containing oeg_up(NH)T dimers. Incorporation of the chimeric synthons into the 3'-end of T-20 brought about growing resistance to 3'-exonucleolytic (SV PDE) cleavage in the order of oeg_t(NH)T < oeg_up(NH)T < oeg_uh(NH)T. Due to different endonuclease activities of 3'- and 5'-exonucleases applied, placing of five consecutive dimers at the 5'-terminus resulted in a relatively smaller, but also side-chain dependent, stabilization towards the hydrolysis by 5'-exonuclease (BS PDE). Neither exonucleases (SV and BS PDE) nor an endonuclease (Nuclease P-1) could hydrolyse the unnatural phosphodiester bond linking the 3'-OH of thymidine to the terminal OH of N-(2-hydroxyethyl)glycine PNA backbone.

  DOI：

  10.1081/ncn-120025243