3,3,3-trifluoro-N-{2-hydroxy-1-[[2-(2-methoxyethoxy)-ethoxy]methyl]ethyl}-2-methoxy-2-phenylpropionamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,3,3-trifluoro-N-{2-hydroxy-1-[[2-(2-methoxyethoxy)-ethoxy]methyl]ethyl}-2-methoxy-2-phenylpropionamide
• 英文别名: (2R)-3,3,3-trifluoro-N-[(2R)-1-hydroxy-3-[2-(2-methoxyethoxy)ethoxy]propan-2-yl]-2-methoxy-2-phenylpropanamide
• 化学式: C₁₈H₂₆F₃NO₆
• 分子量: 409.403
• InChiKey: BZORMSFNAFWJMX-NVXWUHKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-溴-2-(2-甲氧基乙氧基)乙烷 在 N-甲基吗啉 、 sodium hydride 、 N,N-二异丙基乙胺 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 间甲酚 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.5h， 生成 3,3,3-trifluoro-N-{2-hydroxy-1-[[2-(2-methoxyethoxy)-ethoxy]methyl]ethyl}-2-methoxy-2-phenylpropionamide
  参考文献：
  名称：

  Synthesis and Characterization of Conformationally Preorganized, (R)-Diethylene Glycol-Containing γ-Peptide Nucleic Acids with Superior Hybridization Properties and Water Solubility

  摘要：

  Developed in the early 1990s, peptide nucleic acid (PNA) has emerged as a promising class of nucleic acid mimic because of its strong binding affinity and sequence selectivity toward DNA and RNA and resistance to enzymatic degradation by proteases and nucleases; however, the main drawbacks, as compared to other classes of oligonucleotides, are water solubility and biocompatibility. Herein we show that installation of a relatively small, hydrophilic (R)-diethylene glycol ("miniPEG", R-MP) unit at the gamma-backbone transforms a randomly folded PNA into a right-handed helix. Synthesis of optically pure (R-MP)gamma PNA monomers is described, which can be accomplished in a few simple steps from a commercially available and relatively cheap Boc-L-serine. Once synthesized, (R-MP)gamma PNA oligomers are preorganized into a right-handed helix, hybridize to DNA and RNA with greater affinity and sequence selectivity, and are more water soluble and less aggregating than the parental PNA oligomers. The results presented herein have important implications for the future design and application of PNA in biology, biotechnology, and medicine, as well as in other disciplines, including drug discovery and molecular engineering.

  DOI：

  10.1021/jo200482d

文献信息

• Synthesis and Characterization of Conformationally Preorganized, (<i>R</i>)-Diethylene Glycol-Containing γ-Peptide Nucleic Acids with Superior Hybridization Properties and Water Solubility
  作者：Bichismita Sahu、Iulia Sacui、Srinivas Rapireddy、Kimberly J. Zanotti、Raman Bahal、Bruce A. Armitage、Danith H. Ly

  DOI：10.1021/jo200482d

  日期：2011.7.15

  Developed in the early 1990s, peptide nucleic acid (PNA) has emerged as a promising class of nucleic acid mimic because of its strong binding affinity and sequence selectivity toward DNA and RNA and resistance to enzymatic degradation by proteases and nucleases; however, the main drawbacks, as compared to other classes of oligonucleotides, are water solubility and biocompatibility. Herein we show that installation of a relatively small, hydrophilic (R)-diethylene glycol ("miniPEG", R-MP) unit at the gamma-backbone transforms a randomly folded PNA into a right-handed helix. Synthesis of optically pure (R-MP)gamma PNA monomers is described, which can be accomplished in a few simple steps from a commercially available and relatively cheap Boc-L-serine. Once synthesized, (R-MP)gamma PNA oligomers are preorganized into a right-handed helix, hybridize to DNA and RNA with greater affinity and sequence selectivity, and are more water soluble and less aggregating than the parental PNA oligomers. The results presented herein have important implications for the future design and application of PNA in biology, biotechnology, and medicine, as well as in other disciplines, including drug discovery and molecular engineering.