N-(1-thyminylacetyl)-N-(2-((Boc)amino)ethyl)-β-alanine methyl ester | 149376-82-9

• 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-(1-thyminylacetyl)-N-(2-((Boc)amino)ethyl)-β-alanine methyl ester
• CAS: 149376-82-9
• 化学式: C₁₈H₂₈N₄O₇
• 分子量: 412.443
• InChiKey: GJOBRRXTLPSEJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.24
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  139.8
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-(1-thyminylacetyl)-N-(2-((Boc)amino)ethyl)-β-alanine methyl ester 在 sodium hydroxide 作用下， 反应 0.17h， 生成 N-(1-thyminylacetyl)-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-叔丁氧羰基-1,2-乙二胺 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 40.0h， 生成 N-(1-thyminylacetyl)-N-(2-((Boc)amino)ethyl)-β-alanine methyl ester
  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

文献信息

• Triplex‐Forming Peptide Nucleic Acids with Extended Backbones
  作者：Vipin Kumar、Nikita Brodyagin、Eriks Rozners

  DOI：10.1002/cbic.202000432

  日期：2020.12

  PNAs form higher‐stability triple helices with dsRNA than DNA. Structural considerations suggested that extending the PNA backbone by one carbon atom might reverse this preference in favor of DNA; however, experiments disproved this hypothesis. The studies suggested that PNA has an inherent preference for forming A‐form triple‐helical structures and, hence, has higher affinity for RNA than DNA.

  PNA 与 dsRNA 形成比 DNA 稳定性更高的三螺旋。结构考虑表明，将 PNA 主链延长一个碳原子可能会逆转这种偏好，有利于 DNA；然而，实验反驳了这个假设。研究表明，PNA 具有形成 A 型三螺旋结构的内在偏好，因此对 RNA 的亲和力高于 DNA。
• Structure-Activity Studies of the Binding of Modified Peptide Nucleic Acids (PNAs) to DNA
  作者：Birgitte Hyrup、Michael Egholm、Peter E. Nielsen、Pernilla Wittung、Bengt Norden、Ole Buchardt

  DOI：10.1021/ja00097a002

  日期：1994.9

  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.