(2'R,4'R)-2'-(tert-butoxycarbonylaminomethyl)-4'-(thymin-1-yl)-pyrrolidine-1'-yl-acetic acid | 927706-02-3

• 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: (2'R,4'R)-2'-(tert-butoxycarbonylaminomethyl)-4'-(thymin-1-yl)-pyrrolidine-1'-yl-acetic acid
• 英文别名: 2-[(2R,4R)-4-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]acetic acid
• CAS: 927706-02-3
• 化学式: C₁₇H₂₆N₄O₆
• 分子量: 382.417
• InChiKey: NATQQHIPRFRQHF-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2'R,4'R)-2'-(tert-butoxycarbonylaminomethyl)-4'-(thymin-1-yl)-pyrrolidine-1'-yl-acetic acid 、 (2'R,4'R)-2'-[(tert-butoxycarbonyl)aminomethyl]-4'-(N⁶-benzyloxycarbonyladenin-9-yl)-pyrrolidine-1-yl-acetic acid 、 (2'R,4'R)-2'-(tert-butoxycarbonylaminomethyl)-4'-(N⁴-benzyloxycarbonylcytosin-1-yl)-N1'-(methoxycarbonylmethyl)-pyrrolidine-1-yl-acetic acid 、 N-叔丁氧羰基-N'-(2-氯苄氧羰基)-L-赖氨酸 生成 (2S)-2,6-diamino-N-[[(2R,4R)-1-[2-[[(2R,4R)-1-[2-[[(2R,4R)-1-[2-[[(2R,4R)-1-[2-[[(2R,4R)-1-[2-[[(2R,4R)-1-[2-[[(2R,4R)-1-[2-[[(2R,4R)-1-[2-[[(2R,4R)-1-(2-amino-2-oxoethyl)-4-(5-methyl-2,4-dioxopyrimidin-1-yl)pyrrolidin-2-yl]methylamino]-2-oxoethyl]-4-(5-methyl-2,4-dioxopyrimidin-1-yl)pyrrolidin-2-yl]methylamino]-2-oxoethyl]-4-(4-amino-2-oxopyrimidin-1-yl)pyrrolidin-2-yl]methylamino]-2-oxoethyl]-4-(6-aminopurin-9-yl)pyrrolidin-2-yl]methylamino]-2-oxoethyl]-4-(6-aminopurin-9-yl)pyrrolidin-2-yl]methylamino]-2-oxoethyl]-4-(4-amino-2-oxopyrimidin-1-yl)pyrrolidin-2-yl]methylamino]-2-oxoethyl]-4-(6-aminopurin-9-yl)pyrrolidin-2-yl]methylamino]-2-oxoethyl]-4-(4-amino-2-oxopyrimidin-1-yl)pyrrolidin-2-yl]methylamino]-2-oxoethyl]-4-(5-methyl-2,4-dioxopyrimidin-1-yl)pyrrolidin-2-yl]methyl]hexanamide 、 (2S)-2,6-diamino-N-[[(2R,4R)-1-[2-[2-[[2-[[(2R,4R)-1-[2-[2-[[2-[[(2R,4R)-1-[2-[[(2R,4R)-1-[2-[2-[[2-[[(2R,4R)-1-[2-[[(2R,4R)-1-(2-amino-2-oxoethyl)-4-(5-methyl-2,4-dioxopyrimidin-1-yl)pyrrolidin-2-yl]methylamino]-2-oxoethyl]-4-(5-methyl-2,4-dioxopyrimidin-1-yl)pyrrolidin-2-yl]methylamino]-2-oxoethyl]-[2-(4-amino-2-oxopyrimidin-1-yl)acetyl]amino]ethylamino]-2-oxoethyl]-4-(6-aminopurin-9-yl)pyrrolidin-2-yl]methylamino]-2-oxoethyl]-4-(6-aminopurin-9-yl)pyrrolidin-2-yl]methylamino]-2-oxoethyl]-[2-(4-amino-2-oxopyrimidin-1-yl)acetyl]amino]ethylamino]-2-oxoethyl]-4-(6-aminopurin-9-yl)pyrrolidin-2-yl]methylamino]-2-oxoethyl]-[2-(4-amino-2-oxopyrimidin-1-yl)acetyl]amino]ethylamino]-2-oxoethyl]-4-(5-methyl-2,4-dioxopyrimidin-1-yl)pyrrolidin-2-yl]methyl]hexanamide
  参考文献：
  名称：

  Mixed-sequence pyrrolidine-amide oligonucleotide mimics: Boc(Z) synthesis and DNA/RNA binding properties

  摘要：

  吡咯烷酰胺低聚核苷酸模拟物（POMs）展现出了有前景的特性，具有潜在的应用价值，包括体内DNA和RNA靶向、诊断和生物分析。在评估这些应用之前，首先需要合成并确定具有生物学相关混合序列的完全修饰低聚物的性质。因此，制备了Boc-Z保护的胸苷基、腺苷基和胞苷基POM单体，并首次成功用于混合序列POM（Lys-TCACAACTT-NH2）的固相合成。UV热变性研究表明，POM低聚物能够与互补的平行和反平行RNA及DNA链进行序列选择性杂交。尽管双链熔解温度（Tm）高于等序列PNA、DNA和RNA低聚物形成的双链，但混合序列POM与DNA/RNA靶标的结合/解离速率明显较慢。

  DOI：

  10.1039/b613386j
• 作为产物：
  描述：

  (2'R,4'R)-2'-[(tert-butoxycarbonyl)aminomethyl]-4'-(N³-benzoylthymin-1-yl)-N1'-(methoxycarbonylmethyl)-pyrrolidine 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以73%的产率得到(2'R,4'R)-2'-(tert-butoxycarbonylaminomethyl)-4'-(thymin-1-yl)-pyrrolidine-1'-yl-acetic acid
  参考文献：
  名称：

  Mixed-sequence pyrrolidine-amide oligonucleotide mimics: Boc(Z) synthesis and DNA/RNA binding properties

  摘要：

  吡咯烷酰胺低聚核苷酸模拟物（POMs）展现出了有前景的特性，具有潜在的应用价值，包括体内DNA和RNA靶向、诊断和生物分析。在评估这些应用之前，首先需要合成并确定具有生物学相关混合序列的完全修饰低聚物的性质。因此，制备了Boc-Z保护的胸苷基、腺苷基和胞苷基POM单体，并首次成功用于混合序列POM（Lys-TCACAACTT-NH2）的固相合成。UV热变性研究表明，POM低聚物能够与互补的平行和反平行RNA及DNA链进行序列选择性杂交。尽管双链熔解温度（Tm）高于等序列PNA、DNA和RNA低聚物形成的双链，但混合序列POM与DNA/RNA靶标的结合/解离速率明显较慢。

  DOI：

  10.1039/b613386j

文献信息

• Mixed-sequence pyrrolidine-amide oligonucleotide mimics: Boc(Z) synthesis and DNA/RNA binding properties
  作者：Roberta J. Worthington、Adam P. O'Rourke、Jordi Morral、T. H. Samuel Tan、Jason Micklefield

  DOI：10.1039/b613386j

  日期：——

  Pyrrolidine-amide oligonucleotide mimics (POMs) exhibit promising properties for potential applications, including in vivo DNA and RNA targeting, diagnostics and bioanalysis. Before POMs can be evaluated in these applications it is first necessary to synthesise and establish the properties of fully modified oligomers, with biologically relevant mixed sequences. Accordingly, Boc-Z-protected thyminyl, adeninyl and cytosinyl POM monomers were prepared and used in the first successful solid phase synthesis of a mixed sequence POM, Lys-TCACAACTT-NH2. UV thermal denaturation studies revealed that the POM oligomer is capable of hybridising with sequence selectivity to both complementary parallel and antiparallel RNA and DNA strands. Whilst the duplex melting temperatures (Tm) were higher than the corresponding duplexes formed with isosequential PNA, DNA and RNA oligomers the rates of association/dissociation of the mixed sequence POM with DNA/RNA targets were noticeably slower.

  吡咯烷酰胺低聚核苷酸模拟物（POMs）展现出了有前景的特性，具有潜在的应用价值，包括体内DNA和RNA靶向、诊断和生物分析。在评估这些应用之前，首先需要合成并确定具有生物学相关混合序列的完全修饰低聚物的性质。因此，制备了Boc-Z保护的胸苷基、腺苷基和胞苷基POM单体，并首次成功用于混合序列POM（Lys-TCACAACTT-NH2）的固相合成。UV热变性研究表明，POM低聚物能够与互补的平行和反平行RNA及DNA链进行序列选择性杂交。尽管双链熔解温度（Tm）高于等序列PNA、DNA和RNA低聚物形成的双链，但混合序列POM与DNA/RNA靶标的结合/解离速率明显较慢。