(S)-Allyl 2-(N-(2-((tert-butoxycarbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)-5-(3-tosylguanidino)pentanoate | 911286-65-2

• 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: (S)-Allyl 2-(N-(2-((tert-butoxycarbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)-5-(3-tosylguanidino)pentanoate
• 英文别名: prop-2-enyl (2S)-5-[[amino-[(4-methylphenyl)sulfonylamino]methylidene]amino]-2-[[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]pentanoate
• CAS: 911286-65-2
• 化学式: C₃₀H₄₃N₇O₉S
• 分子量: 677.779
• InChiKey: XBBQFIWDZXTKHN-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  47.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  221.85
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (S)-Allyl 2-(N-(2-((tert-butoxycarbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)-5-(3-tosylguanidino)pentanoate 在 吗啉 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (S)-2-(N-(2-((tert-Butoxycarbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)-5-(3-tosylguanidino)pentanoic acid
  参考文献：
  名称：

  Novel Binding and Efficient Cellular Uptake of Guanidine-Based Peptide Nucleic Acids (GPNA)

  摘要：

  Incorporation of a guanidine functional group into the PNA backbone facilitates cellular uptake of PNA into mammalian cells with efficiency comparable to that of the TAT transduction domain. The modified PNA recognizes and binds to the complementary DNA strand in accordance with Watson-Crick recognition rules. However, unlike polypyrimidine PNA which binds to DNA in 2:1 stoichiometry, the modified PNA binds to complementary DNA in a 1:1 ratio to form a highly stable duplex.

  DOI：

  10.1021/ja029665m
• 作为产物：
  描述：

  1-(ethoxycarbonylmethyl)thymine 在 sodium hydroxide 、 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 18.0h， 生成 (S)-Allyl 2-(N-(2-((tert-butoxycarbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)-5-(3-tosylguanidino)pentanoate
  参考文献：
  名称：

  Novel Binding and Efficient Cellular Uptake of Guanidine-Based Peptide Nucleic Acids (GPNA)

  摘要：

  Incorporation of a guanidine functional group into the PNA backbone facilitates cellular uptake of PNA into mammalian cells with efficiency comparable to that of the TAT transduction domain. The modified PNA recognizes and binds to the complementary DNA strand in accordance with Watson-Crick recognition rules. However, unlike polypyrimidine PNA which binds to DNA in 2:1 stoichiometry, the modified PNA binds to complementary DNA in a 1:1 ratio to form a highly stable duplex.

  DOI：

  10.1021/ja029665m