(S)-4-(2-Acetamido-6-oxo-3H-purin-9(6H)-yl)-2-((tert-butoxycarbonyl)amino)butanoic acid | 194920-10-0

• 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: (S)-4-(2-Acetamido-6-oxo-3H-purin-9(6H)-yl)-2-((tert-butoxycarbonyl)amino)butanoic acid
• 英文别名: (2S)-4-(2-acetamido-6-oxo-1H-purin-9-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 194920-10-0
• 化学式: C₁₆H₂₂N₆O₆
• 分子量: 394.387
• InChiKey: XELSCYOHGMERPP-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  164
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-4-(2-Acetamido-6-oxo-3H-purin-9(6H)-yl)-2-((tert-butoxycarbonyl)amino)butanoic acid 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (S)-Ethyl 2-(4-(2-acetamido-6-oxo-3H-purin-9(6H)-yl)-2-((tert-butoxycarbonyl)amino)butanamido)acetate
  参考文献：
  名称：

  α-PNA:  A Novel Peptide Nucleic Acid Analogue of DNA

  摘要：

  Peptide nucleic acid (PNA) analogues of DNA have attracted interest as potential pharmacological regulators of gene expression since they have the capacity to invade duplex DNA forming Watson-Crick base paired PNA:DNA heteroduplexes. Unfortunately, strand invasion is limited to homopurine and homopyrimidine sequences and there is the need to explore further PNA analogues for the purpose of expanding the strand invasion alphabet. Accordingly, we have designed a true peptide mimic of DNA (designated alpha-PNA) involving novel L-alpha-amino acids, with side chains comprising the four DNA bases attached via an ethylene linkage, interspaced with glycine. The four base-containing amino acids have been synthesized from N-Boc-L-homoserine, via alkylation of the appropriate base with the key intermediate (S)-2-(N-Boc-amino)-4-bromobutyric acid methyl ester followed by hydrolysis. These amino acids have been incorporated into alpha-PNA oligomers using both solution and solid phase methods.

  DOI：

  10.1021/jo970111p
• 作为产物：
  描述：

  2-氨基-6-氯嘌呤 在 三乙烯二胺 、 sodium hydroxide 、 potassium carbonate 、 三乙胺 、 四甲基胍 、 2-硝基苯甲醛肟 作用下， 以 1,4-二氧六环 、 吡啶 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.5h， 生成 (S)-4-(2-Acetamido-6-oxo-3H-purin-9(6H)-yl)-2-((tert-butoxycarbonyl)amino)butanoic acid
  参考文献：
  名称：

  α-PNA:  A Novel Peptide Nucleic Acid Analogue of DNA

  摘要：

  Peptide nucleic acid (PNA) analogues of DNA have attracted interest as potential pharmacological regulators of gene expression since they have the capacity to invade duplex DNA forming Watson-Crick base paired PNA:DNA heteroduplexes. Unfortunately, strand invasion is limited to homopurine and homopyrimidine sequences and there is the need to explore further PNA analogues for the purpose of expanding the strand invasion alphabet. Accordingly, we have designed a true peptide mimic of DNA (designated alpha-PNA) involving novel L-alpha-amino acids, with side chains comprising the four DNA bases attached via an ethylene linkage, interspaced with glycine. The four base-containing amino acids have been synthesized from N-Boc-L-homoserine, via alkylation of the appropriate base with the key intermediate (S)-2-(N-Boc-amino)-4-bromobutyric acid methyl ester followed by hydrolysis. These amino acids have been incorporated into alpha-PNA oligomers using both solution and solid phase methods.

  DOI：

  10.1021/jo970111p

文献信息

• α-PNA:  A Novel Peptide Nucleic Acid Analogue of DNA
  作者：Nicola M. Howarth、Laurence P. G. Wakelin

  DOI：10.1021/jo970111p

  日期：1997.8.1

  Peptide nucleic acid (PNA) analogues of DNA have attracted interest as potential pharmacological regulators of gene expression since they have the capacity to invade duplex DNA forming Watson-Crick base paired PNA:DNA heteroduplexes. Unfortunately, strand invasion is limited to homopurine and homopyrimidine sequences and there is the need to explore further PNA analogues for the purpose of expanding the strand invasion alphabet. Accordingly, we have designed a true peptide mimic of DNA (designated alpha-PNA) involving novel L-alpha-amino acids, with side chains comprising the four DNA bases attached via an ethylene linkage, interspaced with glycine. The four base-containing amino acids have been synthesized from N-Boc-L-homoserine, via alkylation of the appropriate base with the key intermediate (S)-2-(N-Boc-amino)-4-bromobutyric acid methyl ester followed by hydrolysis. These amino acids have been incorporated into alpha-PNA oligomers using both solution and solid phase methods.