(S)-5-(benzyloxy)-2-(N-(2-((tert-butoxycarbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)-5-oxopentanoic acid | 888212-77-9

• 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)-5-(benzyloxy)-2-(N-(2-((tert-butoxycarbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)-5-oxopentanoic acid
• CAS: 888212-77-9
• 化学式: C₂₆H₃₄N₄O₉
• 分子量: 546.577
• InChiKey: KOMRLVIYAVGMDZ-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  177.1
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S)-5-(benzyloxy)-2-(N-(2-((tert-butoxycarbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)-5-oxopentanoic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氯化铵 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以71%的产率得到benzyl (S)-5-amino-4-{N-[2-((tert-butoxy)carbonylamino)ethyl]-2-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]-1-oxoethylamino}-5-oxopentanoate
  参考文献：
  名称：

  Peculiarities of solid-phase synthesis of negatively charged chiral polyamides as nucleic acid mimics

  摘要：

  Homopyrimidine polyamide nucleic acid mimics based on L-glutamic acid were prepared by solid-phase synthesis. The effect of the conditions of condensation and cleavage reactions with the use of polymeric support on the yield of the target sequences was studied. Possible ways of formation of by-products were revealed by mass spectrometry.

  DOI：

  10.1134/s1070428013120117

文献信息

• Polyanionic Carboxyethyl Peptide Nucleic Acids (ce-PNAs): Synthesis and DNA Binding
  作者：Yuliya Kirillova、Nataliya Boyarskaya、Andrey Dezhenkov、Mariya Tankevich、Ivan Prokhorov、Anna Varizhuk、Sergei Eremin、Dmitry Esipov、Igor Smirnov、Galina Pozmogova

  DOI：10.1371/journal.pone.0140468

  日期：——

  New polyanionic modifications of polyamide nucleic acid mimics were obtained. Thymine decamers were synthesized from respective chiral α- and γ-monomers, and their enantiomeric purity was assessed. Here, we present the decamer synthesis, purification and characterization by MALDI-TOF mass spectrometry and an investigation of the hybridization properties of the decamers. We show that the modified γ-S-carboxyethyl-T10

  获得了聚酰胺核酸模拟物的新的聚阴离子修饰。从各自的手性α-单体和γ-单体合成胸腺嘧啶十聚体，并评估其对映体纯度。在这里，我们介绍通过MALDI-TOF质谱法对decamer的合成，纯化和表征，以及对decamer杂交特性的研究。我们表明，修饰的γ-S-羧乙基-T10 PNA与聚腺嘌呤DNA形成稳定的三链体。