2-[[(2S)-6-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]-[2-[6-oxo-2-(phenylmethoxycarbonylamino)-1H-purin-9-yl]acetyl]amino]acetic acid | 1118531-69-3

• 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: 2-[[(2S)-6-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]-[2-[6-oxo-2-(phenylmethoxycarbonylamino)-1H-purin-9-yl]acetyl]amino]acetic acid
• CAS: 1118531-69-3
• 化学式: C₄₅H₅₂N₁₀O₁₂
• 分子量: 924.968
• InChiKey: BSKCLOAFTVNGAZ-XIFFEERXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  67
• 可旋转键数：
  26
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  283
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  ethyl 2-[[(2S)-6-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]-[2-[6-oxo-2-(phenylmethoxycarbonylamino)-1H-purin-9-yl]acetyl]amino]acetate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.75h， 以68%的产率得到2-[[(2S)-6-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]-[2-[6-oxo-2-(phenylmethoxycarbonylamino)-1H-purin-9-yl]acetyl]amino]acetic acid
  参考文献：
  名称：

  Synthesis of Conformationally Preorganized and Cell-Permeable Guanidine-Based γ-Peptide Nucleic Acids (γGPNAs)

  摘要：

  A general method for preparing optically pure guanidine-based gamma-peptide nucleic acid (gamma GPNA) monomers for all four natural nucleobases (A, C, G, and T) is described. These second-generation gamma GPNAs differ from the first-generation GPNAs in that the guanidinium group is installed at the gamma- instead of the alpha-position of the N-(2-aminoethyl)glycine backbone unit. This positional switch enables GPNAs to be synthesized from relatively cheap L- as opposed to D-amino acids. Unlike their (x-predecessors, which are randomly folded, gamma GPNAs prepared from L-amino acids are preorganized into a right-handed helix and bind to DNA and RNA with exceptionally high affinity and sequence selectivity and are readily taken up by mammalian cells.

  DOI：

  10.1021/jo802211n