N-(N4-(Z)-1-cytosylacetyl)-N-(2-((Boc)amino)ethyl)-β-alanine methyl ester | 149376-83-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-(N4-(Z)-1-cytosylacetyl)-N-(2-((Boc)amino)ethyl)-β-alanine methyl ester
• 英文别名: N-(N⁴-(Z)-1-cytosylacetyl)-N-(2-((Boc)amino)ethyl)-β-alanine methyl ester
• CAS: 149376-83-0
• 化学式: C₂₅H₃₃N₅O₈
• 分子量: 531.566
• InChiKey: SLRBAARZGFWNPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  158.16
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N-(N4-(Z)-1-cytosylacetyl)-N-(2-((Boc)amino)ethyl)-β-alanine methyl ester 在 sodium hydroxide 作用下， 反应 0.17h， 生成 N-(N⁴-(Z)-1-cytosylacetyl)-N-(2-((Boc)amino)ethyl)-β-alanine
  参考文献：
  名称：

  修饰肽核酸（PNA）的结合亲和力。具有由2-氨乙基-β-丙氨酸或3-氨丙基甘氨酸单元组成的扩展骨架的PNA

  摘要：

  肽核酸（PNA）与DNA之间的结合亲和力通过将PNA单元与扩展的骨架结合而降低。

  DOI：

  10.1039/c39930000518
• 作为产物：
  描述：

  N-CBZ胞嘧啶乙酸 在 三乙胺 、 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 3.0h， 生成 N-(N4-(Z)-1-cytosylacetyl)-N-(2-((Boc)amino)ethyl)-β-alanine methyl ester
  参考文献：
  名称：

  Structure-Activity Studies of the Binding of Modified Peptide Nucleic Acids (PNAs) to DNA

  摘要：

  Peptide nucleic acid (PNA) oligomers where one of the repeating backbone units is extended with a methylene group to either N-(2-aminoethyl)-beta-alanine or N-(3-aminopropyl)glycine were prepared. Alternatively, the linker to the nucleobase was extended from methylenecarbonyl to ethylenecarbonyl. The thermal stability of the hybrids between these PNA oligomers and complementary DNA oligonucleotides was significantly lower than that of the corresponding complexes involving unmodified PNA. However, the sequence selectivity was retained. Thymidyl decamers with all N-(2-aminoethyl)-beta-alanine or N-(3-aminopropyl)glycine backbones were prepared and shown to be unable to hybridize to the complementary (dA)(10) oligonucleotides, whereas a PNA decamer containing only ethylenecarbonyl linkers between the nucleobases and the N-(2-aminoethyl)glycine backbone showed weak but sequence-specific affinity for complementary DNA. All hybrids involving homopyrimidine PNA oligomers exhibited (PNA)(2)/DNA stoichiometry, whereas mixed-sequence PNA oligomers formed PNA/DNA duplexes. The preferred binding direction between the modified PNA and DNA in the duplex motifs was antiparallel, as previously reported for complexes involving unmodified PNA.

  DOI：

  10.1021/ja00097a002