(2'R,4'R)-2'-azidomethyl-4'-(N⁶-benzoyladenin-9-yl)-N1'-(tert-butoxycarbonylmethyl)-pyrrolidine | 718632-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (2'R,4'R)-2'-azidomethyl-4'-(N⁶-benzoyladenin-9-yl)-N1'-(tert-butoxycarbonylmethyl)-pyrrolidine
• CAS: 718632-79-2
• 化学式: C₂₃H₂₇N₉O₃
• 分子量: 477.526
• InChiKey: ZNRYBUGXIPFJOC-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  151.0
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2'R,4'R)-2'-azidomethyl-4'-(N⁶-benzoyladenin-9-yl)-N1'-(tert-butoxycarbonylmethyl)-pyrrolidine 在 吡啶 、 硫化氢 作用下， 反应 18.0h， 生成 (2'R,4'R)-2'-aminomethyl-4'-(N⁶-benzoyladenin-9-yl)-N1'-(tert-butoxycarbonylmethyl)-pyrrolidine
  参考文献：
  名称：

  Nucleic acid binding properties of thyminyl and adeninyl pyrrolidine-amide oligonucleotide mimics (POM)This paper is dedicated to Professor Heinz G. Floss on the occasion of his 70th birthday.Electronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b3/b315768g/

  摘要：

  腺苷-POM 是通过固相肽化学合成的，并显示出相比相应的腺苷-PNA 对互补 DNA 和 RNA 更高的亲和力。

  DOI：

  10.1039/b315768g
• 作为产物：
  描述：

  (2R,4R)-2-azidomethyl-4-hydroxy-N-(tert-butoxycarbonylmethyl)-pyrrolidine 在 吡啶 、 ammonium hydroxide 、 18-冠醚-6 、 偶氮二甲酸二异丙酯 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 (2'R,4'R)-2'-azidomethyl-4'-(N⁶-benzoyladenin-9-yl)-N1'-(tert-butoxycarbonylmethyl)-pyrrolidine
  参考文献：
  名称：

  Nucleic acid binding properties of thyminyl and adeninyl pyrrolidine-amide oligonucleotide mimics (POM)This paper is dedicated to Professor Heinz G. Floss on the occasion of his 70th birthday.Electronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b3/b315768g/

  摘要：

  腺苷-POM 是通过固相肽化学合成的，并显示出相比相应的腺苷-PNA 对互补 DNA 和 RNA 更高的亲和力。

  DOI：

  10.1039/b315768g

文献信息

• Homopolymeric pyrrolidine-amide oligonucleotide mimics: Fmoc-synthesis and DNA/RNA binding properties
  作者：T. H. Samuel Tan、Roberta J. Worthington、Robin G. Pritchard、Jordi Morral、Jason Micklefield

  DOI：10.1039/b613384n

  日期：——

  By chemically modifying or replacing the backbone of oligonucleotides it is possible to modulate the DNA and RNA recognition properties and fine-tune the physiochemical properties of oligomers. This is important because it challenges our understanding of natural nucleic acid structural and recognition properties and can lead to nucleic acid mimics with a wide range of applications in nucleic acid targeting, analysis or diagnostics. In this paper we describe the solid phase synthesis of pyrrolidine-amide oligonucleotide mimics (POMs) using Fmoc-peptide chemistry. This required the synthesis of adeninyl, cytosinyl, thyminyl and guaninyl pyrrolidine monomers, with Fmoc- and standard acyl-protecting groups on the exocyclic amino groups and nucleobases respectively. These monomers were used to synthesise several thyminyl and adeninyl POM pentamers, with modest coupling efficiency. The pentamers were purified by RP-HPLC, characterised by mass spectrometry and their DNA and RNA binding properties were investigated using UV thermal denaturation/renaturation experiments. This revealed that all the pentamers exhibit strong affinity for complementary nucleic acids. The further evaluation of longer mixed-sequence POMs is described in a second accompanying paper (R. J. Worthington et al., Org. Biomol. Chem., 2006, DOI: 10.1039/b613386j).

  通过化学修饰或替换寡核苷酸的主链，可以调节其对DNA和RNA的识别特性，并精细调整寡聚物的物理化学性质。这一点之所以重要，是因为它挑战了我们对天然核酸结构和识别特性的理解，并可能导致开发出一系列在核酸靶向、分析或诊断方面有广泛应用的核酸类似物。本文描述了使用Fmoc肽化学的吡咯烷酰胺寡核苷酸类似物（POMs）的固相合成。这需要合成腺苷基、胞苷基、胸苷基和鸟苷基吡咯烷单体，吡咯烷环外氨基分别带有Fmoc保护基团和标准酰基保护基团。这些单体被用于合成数种胸苷基和腺苷基POM五聚体，其偶联效率一般。五聚体通过RP-HPLC进行纯化，通过质谱法进行表征，并使用紫外光热变性/复性实验研究其与DNA和RNA的结合特性。结果显示，所有五聚体都显示出对互补核酸的强烈亲和力。对更长的混合序列POMs的进一步评估在另一篇伴随论文中描述（R. J. Worthington等，Org. Biomol. Chem., 2006, DOI: 10.1039/b613386j）。