5-(3-azidopropylamino)-5-oxopentanoic acid | 510758-33-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-(3-azidopropylamino)-5-oxopentanoic acid
• 英文别名: 4-(3-azidopropylcarbamoyl)butyric acid；(3-azidopropylcarbamoyl)butyric acid；5-(3-Azidopropylamino)-5-oxopentanoic acid
• CAS: 510758-33-5
• 化学式: C₈H₁₄N₄O₃
• 分子量: 214.224
• InChiKey: UPZALMCPRFZBAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  80.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(3-azidopropylamino)-5-oxopentanoic acid 在 吡啶 、 铜 、 copper(II) sulfate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 phosphate buffer 、 乙醇 、 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Adding Amino Acids with Novel Reactivity to the Genetic Code of Saccharomyces Cerevisiae

  摘要：

  Using a novel genetic selection, we have identified a series of mutants of the E. coli tyrosyl-tRNA synthetase that selectively charge an amber suppressor tRNA with p-(propargyloxy)phenylalanine and p-azidophenylalanine in yeast. These evolved tRNA-synthetase pairs can be used to site-specifically label proteins with functional groups orthogonal to normal biological chemistries. As an example, we have shown that proteins containing these amino acids can be efficiently bioconjugated with small organic molecules by a [3 + 2] cycloaddition reaction that is mild enough for the manipulation of biological samples.

  DOI：

  10.1021/ja0370037
• 作为产物：
  描述：

  戊二酸酐 、 3-叠氮基丙胺 以 二氯甲烷 为溶剂， 以100%的产率得到5-(3-azidopropylamino)-5-oxopentanoic acid
  参考文献：
  名称：

  Bioconjugation by Copper(I)-Catalyzed Azide-Alkyne [3 + 2] Cycloaddition

  摘要：

  The copper-catalyzed cycloaddition reaction between azides and alkynes functions efficiently in aqueous solution in the presence of a tris(triazolyl)amine ligand. The process has been employed to make rapid and reliable covalent connections to micromolar concentrations of protein decorated with either of the reactive moieties. The chelating ligand plays a crucial role in stabilizing the Cu(I) oxidation state and protecting the protein from Cu(triazole)-induced denaturation. Because the azide and alkyne groups themselves are unreactive with protein residues or other biomolecules, their ligation is of potential utility as a general bioconjugation method.

  DOI：

  10.1021/ja021381e

文献信息

• Compositions and methods for coupling a plurality of compounds to a scaffold
  申请人：The Scripps Research Institute

  公开号：EP2452936A1

  公开（公告）日：2012-05-16

  Compositions and methods are provided for coupling a plurality of compounds to a scaffold. Compositions and methods are further provided for catalyzing a reaction between at least one terminal alkyne moiety and at least one azide moiety, wherein one moiety is attached to the compound and the other moiety is attached to the scaffold, forming at least one triazole thereby.

  本发明提供了将多种化合物耦合到支架上的组合物和方法。本发明还提供了在至少一个末端炔基团与至少一个叠氮基团之间催化反应的组合物和方法，其中一个基团附着在化合物上，另一个基团附着在支架上，从而形成至少一种三唑类化合物。
• Virus–glycopolymer conjugates by copper(i) catalysis of atom transfer radical polymerization and azide–alkyne cycloaddition
  作者：Sayam Sen Gupta、Krishnaswami S. Raja、Eiton Kaltgrad、Erica Strable、M. G. Finn

  DOI：10.1039/b502444g

  日期：——

  The CuI-catalyzed ATRP and azide–alkyne cycloaddition reactions together provide a versatile method for the synthesis of end-functionalized glycopolymers and their attachment to a suitably modified viral protein scaffold.

  CuI 催化的 ATRP 反应和叠氮烷烃环加成反应为合成末端官能化的糖聚合物并将其连接到适当修饰的病毒蛋白质支架上提供了一种多功能方法。
• Expanding the eukaryotic genetic code
  申请人：Chin W. Jason

  公开号：US20050009049A1

  公开（公告）日：2005-01-13

  This invention provides compositions and methods for producing translational components that expand the number of genetically encoded amino acids in eukaryotic cells. The components include orthogonal tRNAs, orthogonal aminoacyl-tRNA synthetases, orthogonal pairs of tRNAs/synthetases and unnatural amino acids. Proteins and methods of producing proteins with unnatural amino acids in eukaryotic cells are also provided.

  本发明提供了一种用于生产转录组件的组合物和方法，该组合物可以扩展真核细胞中遗传编码的氨基酸数量。该组件包括正交tRNA，正交氨酰-tRNA合成酶，正交tRNA/合成酶对和非天然氨基酸。还提供了在真核细胞中使用非天然氨基酸生产蛋白质的方法和蛋白质。
• Unnatural reactive amino acid genetic code additions
  申请人：The Scripps Research Institute

  公开号：US20040265952A1

  公开（公告）日：2004-12-30

  This invention provides compositions and methods for producing translational components that expand the number of genetically encoded amino acids in eukaryotic cells. The components include orthogonal tRNAs, orthogonal aminoacyl-tRNA synthetases, orthogonal pairs of tRNAs/synthetases and unnatural amino acids. Proteins and methods of producing proteins with unnatural amino acids in eukaryotic cells are also provided.

  本发明提供了组成物和方法，用于生产翻译组分，以扩展真核细胞中基因编码的氨基酸数量。这些组分包括正交的tRNA、正交的氨酰-tRNA合成酶、正交的tRNA/合成酶对和非天然氨基酸。还提供了在真核细胞中生产带有非天然氨基酸的蛋白质和生产蛋白质的方法。
• Expanding the Eukaryotic Genetic Code
  申请人：Chin Jason W.

  公开号：US20120253026A1

  公开（公告）日：2012-10-04

  This invention provides compositions and methods for producing translational components that expand the number of genetically encoded amino acids in eukaryotic cells. The components include orthogonal tRNAs, orthogonal aminoacyl-tRNA synthetases, orthogonal pairs of tRNAs/synthetases and unnatural amino acids. Proteins and methods of producing proteins with unnatural amino acids in eukaryotic cells are also provided.

  本发明提供了用于生产转录组件的组合物和方法，这些组合物可以扩大真核细胞中遗传编码的氨基酸数量。这些组件包括正交的tRNA，正交的氨酰-tRNA合成酶，正交的tRNA/合成酶对和非天然氨基酸。本发明还提供了在真核细胞中产生带有非天然氨基酸的蛋白质和制造蛋白质的方法。