Boc-Lys{(guanidine-di-Cbz)-ψ[CH2N]}Gly-OEt | 1118531-53-5

• 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: Boc-Lys{(guanidine-di-Cbz)-ψ[CH2N]}Gly-OEt
• 英文别名: ethyl 2-[[(2S)-6-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]amino]acetate
• CAS: 1118531-53-5
• 化学式: C₃₂H₄₅N₅O₈
• 分子量: 627.738
• InChiKey: FSJITYOBHIGKNT-SANMLTNESA-N

物化性质

• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  45
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  166
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Boc-Lys{(guanidine-di-Cbz)-ψ[CH2N]}Gly-OEt 、 [6-N-(benzyloxycarbonyl)-adenin-9-yl]-acetic acid 在 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以85%的产率得到ethyl 2-[[(2S)-6-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]-[2-[6-(phenylmethoxycarbonylamino)purin-9-yl]acetyl]amino]acetate
  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：

  Boc-Lys{(guanidine-di-Cbz)-ψ[CH2N(o,p-diNBS)]}Gly-OEt 在 正丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以76%的产率得到Boc-Lys{(guanidine-di-Cbz)-ψ[CH2N]}Gly-OEt
  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.