N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N(1)-acetyl)-glycine ethyl ester)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine | 287487-40-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N(1)-acetyl)-glycine ethyl ester)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine
• 英文别名: ethyl 2-[2-[[[[(2R,3S,5R)-2-[[[(4-methoxyphenyl)-diphenylmethyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]amino]-(2,2,2-trichloroethoxycarbonylamino)methylidene]amino]ethyl-[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]amino]acetate
• CAS: 287487-40-5
• 化学式: C₄₇H₅₂Cl₃N₉O₁₁
• 分子量: 1025.34
• InChiKey: CHBQZOJNJJFFNQ-QOZRZDGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  70.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  249.54
• 氢给体数：
  5.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N(1)-acetyl)-glycine ethyl ester)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以79.3%的产率得到N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N(1)-acetyl)-glycine)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine
  参考文献：
  名称：

  Deoxynucleic Guanidine/Peptide Nucleic Acid Chimeras:  Synthesis, Binding and Invasion Studies with DNA

  摘要：

  A fully automated solid-phase synthetic procedure for incorporation of positively charged guanidinium linkages into otherwise neutral PNA sequences has been employed. These DNG/PNA chimeras form [(DNG/PNA)(2). DNA] triplexes upon binding to single strand or duplex DNA (with accompanying D-loop for the latter). The [(DNG/PNA)(2) . DNA] triplexes of DNG/PNA T-10, with DNA dA(10), are more stable than DNA DNA triplexes [(T-10)(2). dA(10)]. The binding of DNG/PNA chimera with guanidinium linkages on both ends, with single strand length-matched complementary DNA under thermal melt conditions and with longer double strand DNA under isothermal conditions is sequence specific. The association process of DNG/PNA chimera with single strand DNA and strand invasion of longer ds-DNA is faster than the association of PNA, with the same DNA targets, as evident by thermal hysteresis and gel retardation under isothermal conditions. The sequence specific and faster strand invasion of DNG/PNA may extend the potential utility of PNA in diagnostics, biomolecular probes, and antisense/antigene therapeutics.

  DOI：

  10.1021/ja000022l
• 作为产物：
  描述：

  Ethyl 2-(N-(2-aminoethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetate 在 TEA 、 N,N-二异丙基乙胺 、 mercury dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N(1)-acetyl)-glycine ethyl ester)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine
  参考文献：
  名称：

  Deoxynucleic Guanidine/Peptide Nucleic Acid Chimeras:  Synthesis, Binding and Invasion Studies with DNA

  摘要：

  A fully automated solid-phase synthetic procedure for incorporation of positively charged guanidinium linkages into otherwise neutral PNA sequences has been employed. These DNG/PNA chimeras form [(DNG/PNA)(2). DNA] triplexes upon binding to single strand or duplex DNA (with accompanying D-loop for the latter). The [(DNG/PNA)(2) . DNA] triplexes of DNG/PNA T-10, with DNA dA(10), are more stable than DNA DNA triplexes [(T-10)(2). dA(10)]. The binding of DNG/PNA chimera with guanidinium linkages on both ends, with single strand length-matched complementary DNA under thermal melt conditions and with longer double strand DNA under isothermal conditions is sequence specific. The association process of DNG/PNA chimera with single strand DNA and strand invasion of longer ds-DNA is faster than the association of PNA, with the same DNA targets, as evident by thermal hysteresis and gel retardation under isothermal conditions. The sequence specific and faster strand invasion of DNG/PNA may extend the potential utility of PNA in diagnostics, biomolecular probes, and antisense/antigene therapeutics.

  DOI：

  10.1021/ja000022l