N-(1-thyminyl-3-propanoyl)-N-(2-((Boc)amino)ethyl)glycine ethyl ester | 149376-79-4

• 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: N-(1-thyminyl-3-propanoyl)-N-(2-((Boc)amino)ethyl)glycine ethyl ester
• 英文别名: N-(N'-BOC-aminoethyl)-N-[(1-thyminyl)-propanoyl]glycine ethyl ester；ethyl 2-[3-(5-methyl-2,4-dioxopyrimidin-1-yl)propanoyl-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]acetate
• CAS: 149376-79-4
• 化学式: C₁₉H₃₀N₄O₇
• 分子量: 426.47
• InChiKey: VRMZUPJIHDFRQE-UHFFFAOYSA-N

物化性质

• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(1-thyminyl-3-propanoyl)-N-(2-((Boc)amino)ethyl)glycine ethyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以99%的产率得到N-(1-thyminyl-3-propanoyl)-N-(2-((Boc)amino)ethyl)glycine
  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
• 作为产物：
  描述：

  3-(1-thyminyl)propanoic acid methyl ester 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-(1-thyminyl-3-propanoyl)-N-(2-((Boc)amino)ethyl)glycine ethyl 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

文献信息

• Peptide nucleic acids
  申请人：——

  公开号：US20030180734A1

  公开（公告）日：2003-09-25

  A novel class of compounds, known as peptide nucleic acids, bind complementary ssDNA and RNA strands more strongly than a corresponding DNA. The peptide nucleic acids generally comprise ligands such as naturally occurring DNA bases attached to a peptide backbone through a suitable linker.

  一种新型化合物被称为肽核酸，与互补的单链DNA和RNA比相应的DNA更强烈地结合。肽核酸通常包括配体，如天然存在的DNA碱基，通过适当的连接剂连接到肽骨架上。
• Peptide nucleic acids and synthetic procedures therefor
  申请人：Buchardt Ole

  公开号：US20050009041A1

  公开（公告）日：2005-01-13

  A novel class of compounds, known as peptide nucleic acids, bind complementary ssDNA and RNA strands more strongly than a corresponding DNA. The peptide nucleic acids generally comprise ligands such as naturally occurring DNA bases attached to a peptide backbone through a suitable linker.

  一种新型化合物，被称为肽核酸，能够比相应的DNA更强烈地结合互补的单链DNA和RNA。肽核酸通常包括配体，如天然存在的DNA碱基，通过适当的连接剂连接到肽骨架上。
• Use of nucleic acid analogues in diagnostics and analytical procedures
  申请人：Buchardt Ole

  公开号：US20060046255A1

  公开（公告）日：2006-03-02

  The present invention pertains to certain nucleic acid analogs and related kits that are useful for the capture, recognition, detection, identification, or quantification of certain chemical or biological entities.

  本发明涉及某些核酸类似物和相关工具包，这些工具包用于捕获、识别、检测、鉴定或定量化某些化学或生物实体。
• Peptide nucleic acids having 2,6-diaminopurine nucleobases
  申请人：——

  公开号：US20020146718A1

  公开（公告）日：2002-10-10

  A novel class of compounds, known as peptide nucleic acids, bind complementary DNA and RNA strands more strongly than a corresponding DNA strand, and exhibit increased sequence specificity and binding affinity. The peptide nucleic acids of the invention comprise ligands selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases attached to a polyamide backbone. Some PNAs of the invention also contain C 1 -C 8 alkylamine side chains.

  一种新型化合物被称为肽核酸，它们比相应的DNA链和RNA链更强地结合互补的DNA和RNA链，并表现出增加的序列特异性和结合亲和力。该发明的肽核酸包括从天然存在的碱基和连接到聚酰胺骨架的非天然存在的碱基中选择的配体。该发明的一些肽核酸还含有C1-C8烷基胺侧链。
• Peptide nucleic acids having amino acid side chains
  申请人：——

  公开号：US05719262A1

  公开（公告）日：1998-02-17

  A novel class of compounds, known as peptide nucleic acids, bind complementary DNA and RNA strands more strongly than the corresponding DNA or RNA strands, and exhibit increased sequence specificity and solubility. The peptide nucleic acids comprise ligands selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases attached to a polyamide backbone, and contain alkylamine side chains.

  一种新型化合物被称为肽核酸，它比相应的DNA或RNA链更强地结合互补的DNA和RNA链，并表现出增强的序列特异性和溶解性。肽核酸包括从一组中选择的配体，该组包括天然存在的核碱基和附加到聚酰胺骨架上的非天然存在的核碱基，并含有烷基胺侧链。