(S)-2-[N-(tert-butoxycarbonyl)amino]-4-(thymin-1-yl)butyric acid | 165266-76-2

• 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)-2-[N-(tert-butoxycarbonyl)amino]-4-(thymin-1-yl)butyric acid
• 英文别名: (S)-2-((tert-Butoxycarbonyl)amino)-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)butanoic acid；(2S)-4-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 165266-76-2
• 化学式: C₁₄H₂₁N₃O₆
• 分子量: 327.337
• InChiKey: MXGGHQQNCDRRQY-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-[N-(tert-butoxycarbonyl)amino]-4-(thymin-1-yl)butyric acid 在 sodium hydroxide 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 [(S)-2-tert-Butoxycarbonylamino-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butyrylamino]-acetic 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
• 作为产物：
  描述：

  N-叔丁氧羰基-L-谷氨酸 1-苄酯 在 palladium(II) oxide N-乙基吗啉 、 三氯溴甲烷 、 氢气 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.17h， 生成 (S)-2-[N-(tert-butoxycarbonyl)amino]-4-(thymin-1-yl)butyric acid
  参考文献：
  名称：

  丙氨酰肽核酸的侧链同源性：配对选择性和堆积。

  摘要：

  丙氨酰肽核酸（丙氨酰-PNA）是基于规则的肽主链和氨基酸的交替构型的寡聚体。所有侧链均被共价连接的核碱基修饰。基于互补链的氢键键合，堆积和溶剂化，丙氨酰-PNAs形成非常刚性，定义明确且线性的双链。通过比较亚甲基接头（丙氨酰基-PNA）与乙烯接头（同丙氨酰基-PNA），三亚甲基接头（降冰片基-PNA）和PNA序列（核碱基和主链之间的接头长度混合）来检查侧链同源性。侧链同源性与线性双链拓扑结构相结合，对于选择性地选择配对选择性（配对模式）和碱基对堆积非常有价值。

  DOI：

  10.1039/b411545g

文献信息

• Synthesis of N-Boc-α-amino acids with nucleobase residues as building blocks for the preparation of chiral PNA (peptidic nucleic acids)
  作者：Alessandro Lenzi、Gianna Reginato、Maurizio Taddai

  DOI：10.1016/0040-4039(95)00052-e

  日期：1995.3

  N-Boc-Glutamic acid α-benzyl ester was transformed into 4-bromo-2-(tert-butoxycarbonylamino)-butyric acid benzyl ester using the Barton-Crich protocol. This bromo derivative undergoes nucleophilic substitution with nucleobases to give optically active N-Boc-4-adeninbutyrine (Boc-Aby), N-Boc-4-thyminbutyrine (Boc-Tby), N-Boc-4-guaninbutyrine (Boc-Gby) or N-Boc-4-cytosinbutyrine (Boc-Cby), useful building

  使用Barton-Crich方案将N-Boc-谷氨酸α-苄基酯转化为4-溴-2-（叔丁氧基羰基氨基）-丁酸苄基酯。该溴代衍生物经核碱基进行亲核取代，得到旋光的N-Boc-4-腺嘌呤丁胺（Boc-Aby），N-Boc-4-胸腺嘧啶（Boc-Tby），N-Boc-4-鸟嘌呤丁胺（Boc-Gby）或N-Boc-4-cytosinbutyrine（Boc-Cby），它们是合成手性肽核酸（PNA）的有用组成部分。
• Peptide Analogues of DNA Consisting of l-α-Amino-γ-thymine Butyric Acid and l-Valine Subunits
  作者：G. Ceulemans、K. Khan、A. Van Schepdael、P. Herdewijn

  DOI：10.1080/15257779508012478

  日期：1995.5.1

  Reaction of N-Boc-L-homoserine benzylester with N-3-benzoylthymine under Mitsunobu conditions afforded N-Boc-L-alpha-amino-gamma-N-3-benzoylthymine butyric acid benzylester. After removal of the N-benzoyl and O-benzyl protecting group, this compound was used in solution phase peptide synthesis.