2-[[(2S)-6-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]-[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]amino]acetic acid | 1118531-64-8

• 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-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]amino]acetic acid
• CAS: 1118531-64-8
• 化学式: C₃₇H₄₇N₇O₁₁
• 分子量: 765.82
• InChiKey: XOVPNQLTLLLRBZ-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  55
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  234
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-[[(2S)-6-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]-[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]amino]acetic acid 在 间甲酚 、 三氟乙酸 作用下， 以99%的产率得到2-[[(2S)-2-amino-6-[bis(phenylmethoxycarbonylamino)methylideneamino]hexyl]-[2-(5-methyl-2,4-dioxopyrimidin-1-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
• 作为产物：
  描述：

  ethyl 2-[[(2S)-6-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]-[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]amino]acetate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.75h， 以72%的产率得到2-[[(2S)-6-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]-[2-(5-methyl-2,4-dioxopyrimidin-1-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

文献信息

• Synthesis of Conformationally Preorganized and Cell-Permeable Guanidine-Based γ-Peptide Nucleic Acids (γGPNAs)
  作者：Bichismita Sahu、Venugopal Chenna、Kira L. Lathrop、Sufi M. Thomas、Gerald Zon、Kenneth J. Livak、Danith H. Ly

  DOI：10.1021/jo802211n

  日期：2009.2.20

  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.