(S)-N-tert-butoxycarbonyl-γ-(N4-benzoxycarbonyl-1-cytosinyl)homoalanine | 168264-14-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-tert-butoxycarbonyl-γ-(N4-benzoxycarbonyl-1-cytosinyl)homoalanine
• 英文别名: (S)-4-(4-(((Benzyloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)-2-((tert-butoxycarbonyl)amino)butanoic acid；(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-[2-oxo-4-(phenylmethoxycarbonylamino)pyrimidin-1-yl]butanoic acid
• CAS: 168264-14-0
• 化学式: C₂₁H₂₆N₄O₇
• 分子量: 446.46
• InChiKey: BEJZRPGHIUPIPM-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  147
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-N-tert-butoxycarbonyl-γ-(N4-benzoxycarbonyl-1-cytosinyl)homoalanine 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 [(S)-2-Amino-4-(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-butyrylamino]-acetic acid ethyl ester; compound with trifluoro-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：

  (S)-2-tert-Butoxycarbonylamino-pentanedioic acid 1-benzyl ester 5-(2-thioxo-2H-pyridin-1-yl) ester 在 三氯溴甲烷 、 Chirazyme P-1 、 potassium carbonate 作用下， 以 phosphate buffer 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 20.0h， 生成 (S)-N-tert-butoxycarbonyl-γ-(N4-benzoxycarbonyl-1-cytosinyl)homoalanine
  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

• Metal Binding Within a Peptide‐Based Nucleobase Stack with Tuneable Double‐Strand Topology
  作者：Andrea Küsel、Jinhua Zhang、Miguel Alvariño Gil、A. Claudia Stückl、Wolfram Meyer‐Klaucke、Franc Meyer、Ulf Diederichsen

  DOI：10.1002/ejic.200500464

  日期：2005.11

  Peptide nucleic acid (PNA) oligomers with linear topology are synthesised with histidines at the central positions in order to provide metal-ion coordination sites within the water shielded and non-polar environment of a nucleobase stack that emerges upon duplex formation. Variation of the linker length used for attachment of the nucleobases to the regular peptide backbone allows for fine tuning of

  具有线性拓扑结构的肽核酸 (PNA) 寡聚体在中心位置与组氨酸合成，以便在双链体形成时出现的核碱基堆栈的水屏蔽和非极性环境中提供金属离子配位位点。用于将核碱基连接到常规肽主链的接头长度的变化允许微调金属结合位点的距离和配位环境。锌和铜掺入改性丙氨酰-PNA 支架对双链稳定性的影响通过温度依赖性紫外光谱进行了探测，并从 EPR 光谱和 EXAFS 中获得了额外的见解。每当有四个组氨酸（每个寡聚体链两个）可用时，添加 Zn2+ 显着增强双链稳定性，因此支持 Zn2+ 与组氨酸-N 的配位和金属离子在基体中的结合。然而，与 Zn2+ 相比，Cu2+ 离子不会诱导丙氨酰/正缬氨酰-PNA 低聚物的双链形成，正如 EPR 和 EXAFS 所证实的，这表明混合 N2Ox} 供体环境。虽然金属离子与组氨酸修饰的丙氨酰-PNA 低聚物（和同系物）结合显然是可行的，但结合位点几何形状和特定金属离子的立体电
• PERFLUORINATED COMPOUNDS FOR THE NON-VIRAL TRANSFER OF NUCLEIC ACIDS
  申请人：Schäfer Konstanze

  公开号：US20140065223A1

  公开（公告）日：2014-03-06

  The invention relates to a compound of general formula (I): A-B-C(F, G′)-D-E-F-G-A′ or a structure of general formula (II): A-B-C-(F′, G′)-D-B-E-F-G-A′ (II), wherein -A is at least one molecule selected from the group of the perfluorocarbons (PFCs), perfluorinated silicon compounds, and/or further perfluorinated compounds, -B is at least one predetermined breaking point in the form of a physically, chemically, or enzymatically severable bond, -C is absent or at least one linker molecule, -D is absent or at least one spacer molecule, -E is at least one molecule selected from the group containing nucleobases, nucleosides, nucleotides, oligonucleotides, nucleic, acids, modified nucleobases, modified nucleosides, modified nucleotides, modified oligonucleotides, modified nucleic acids, monomers of peptide nucleic acids, oligomers or peptide nucleic acids and peptide nucleic acids or other nucleic acid analogs, -F, F′ is absent or at least one ligand, -G, G′ is absent or at least one marker molecule, -A′ is absent or has the meaning of A, and wherein the compounds i), ii), iii), iv), v), vi) are excluded. The invention farther relates to the use of said compound for the non-viral transfer of molecule E into a cell, to a pharmaceutical composition containing said compound, and to the use of said pharmaceutical composition.
• Side chain homologation of alanyl peptide nucleic acids: pairing selectivity and stacking
  作者：Ulf Diederichsen、Daniel Weicherding、Nicola Diezemann

  DOI：10.1039/b411545g

  日期：——

  Alanyl peptide nucleic acids (alanyl-PNAs) are oligomers based on a regular peptide backbone with alternating configuration of the amino acids. All side chains are modified by covalently linked nucleobases. Alanyl-PNAs form very rigid, well defined, and linear double strands based on hydrogen bonding of complementary strands, stacking, and solvation. Side chain homology was examined by comparing a

  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。
• 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.