(S)-Methyl 4-(6-amino-9H-purin-9-yl)-2-((tert-butoxycarbonyl)amino)butanoate | 177024-64-5

• 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)-Methyl 4-(6-amino-9H-purin-9-yl)-2-((tert-butoxycarbonyl)amino)butanoate
• 英文别名: methyl (2S)-4-(6-aminopurin-9-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 177024-64-5
• 化学式: C₁₅H₂₂N₆O₄
• 分子量: 350.377
• InChiKey: HXLBPKWSNYPGHU-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-Methyl 4-(6-amino-9H-purin-9-yl)-2-((tert-butoxycarbonyl)amino)butanoate 在 sodium hydroxide 、 triethyloxonium fluoroborate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 ((S)-4-(6-Benzyloxycarbonylamino-purin-9-yl)-2-{2-[(S)-4-(6-benzyloxycarbonylamino-purin-9-yl)-2-tert-butoxycarbonylamino-butyrylamino]-acetylamino}-butyrylamino)-acetic acid ethyl ester
  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：

  N-[(1,1-二甲基乙氧基)羰基]-l-高丝氨酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 三苯基膦 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-Methyl 4-(6-amino-9H-purin-9-yl)-2-((tert-butoxycarbonyl)amino)butanoate
  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.