N-hydroxysuccinimidyl 11-(pyrrol-1-yl)-undecanoate | 848074-61-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-hydroxysuccinimidyl 11-(pyrrol-1-yl)-undecanoate
• 英文别名: 1-(11-succinimidyloxycarbonylundecenyl)pyrrole；(2,5-Dioxopyrrolidin-1-yl) 11-pyrrol-1-ylundecanoate；(2,5-dioxopyrrolidin-1-yl) 11-pyrrol-1-ylundecanoate
• CAS: 848074-61-3
• 化学式: C₁₉H₂₈N₂O₄
• 分子量: 348.442
• InChiKey: GJCQKGSFCVMUAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  472.9±37.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-hydroxysuccinimidyl 11-(pyrrol-1-yl)-undecanoate 在 肼 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 11-(pyrrol-1-yl)-undecanoyl-hydrazide
  参考文献：
  名称：

  Polypyrrole Oligosaccharide Array and Surface Plasmon Resonance Imaging for the Measurement of Glycosaminoglycan Binding Interactions

  摘要：

  为了构建能够筛选寡糖-蛋白质相互作用的工具，我们开发了一种基于聚吡咯的寡糖芯片，它是通过吡咯和吡咯修饰寡糖的共聚过程构建而成的。在我们的研究中，参与许多基本生物过程的 GAG（糖胺聚糖）或 GAG 片段被吡咯分子修饰其还原端，然后固定在芯片上。通过表面等离子体共振成像（SPRi），可以同时实时监测和量化表面上侧的平行结合事件，而无需标记。我们的研究表明，在金表面上对低聚糖-吡咯进行电聚合，可以共价固定多个探针，然后利用表面等离子体共振成像技术监测它们的结合能力。此外，在生物应用中，不同的 GAG 片段和不同的蛋白质（包括基质细胞衍生因子-1α（SDF-1α）、干扰素-γ（IFN-γ）和单克隆抗体）显示出不同的亲和模式。

  DOI：

  10.1021/ac800226k
• 作为产物：
  描述：

  11-氨基十一酸 在 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 N-hydroxysuccinimidyl 11-(pyrrol-1-yl)-undecanoate
  参考文献：
  名称：

  Electrogeneration of a Poly(pyrrole)-NTA Chelator Film for a Reversible Oriented Immobilization of Histidine-Tagged Proteins

  摘要：

  This contribution reports, for the first time, the synthesis and electropolymerization of a pyrrole N-substituted by a nitrilotriacetic acid acting as a chelating center of Cu2+. A step-by-step approach for protein immobilization was developed via the successive coordination of Cu2+ and histidine-tagged proteins. The self-assembly of histidine-tagged glucose oxidase led to the formation of a close-packed enzyme monolayer at the poly(pyrrole) surface, and the reversibility and reproducibility of this affinity process were demonstrated.

  DOI：

  10.1021/ja050390v

文献信息

• Electrogeneration of a Poly(pyrrole)-NTA Chelator Film for a Reversible Oriented Immobilization of Histidine-Tagged Proteins
  作者：Naoufel Haddour、Serge Cosnier、Chantal Gondran

  DOI：10.1021/ja050390v

  日期：2005.4.1

  This contribution reports, for the first time, the synthesis and electropolymerization of a pyrrole N-substituted by a nitrilotriacetic acid acting as a chelating center of Cu2+. A step-by-step approach for protein immobilization was developed via the successive coordination of Cu2+ and histidine-tagged proteins. The self-assembly of histidine-tagged glucose oxidase led to the formation of a close-packed enzyme monolayer at the poly(pyrrole) surface, and the reversibility and reproducibility of this affinity process were demonstrated.
• Polypyrrole Oligosaccharide Array and Surface Plasmon Resonance Imaging for the Measurement of Glycosaminoglycan Binding Interactions
  作者：Emilie Mercey、Rabia Sadir、Emmanuel Maillart、André Roget、Françoise Baleux、Hugues Lortat-Jacob、Thierry Livache

  DOI：10.1021/ac800226k

  日期：2008.5.1

  In order to construct tools able to screen oligosaccharide−protein interactions, we have developed a polypyrrole-based oligosaccharide chip constructed via a copolymerization process of pyrrole and pyrrole-modified oligosaccharide. For our study, GAG (glycosaminoglycans) or GAG fragments, which are involved in many fundamental biological processes, were modified by the pyrrole moiety on their reducing end and then immobilized on the chip. The parallel binding events on the upperside of the surface can be simultaneously monitored and quantified in real time and without labeling by surface plasmon resonance imaging (SPRi). We show that electrocopolymerization of the oligosaccharide−pyrrole above a gold surface enables the covalent immobilization of multiple probes and the subsequent monitoring of their binding capacities using surface plasmon resonance imaging. Moreover, a biological application was made involving different GAG fragments and different proteins, including stromal cell-derived factor-1α (SDF-1α), interferon-γ (IFN-γ), and monoclonal antibody showing different affinity pattern.

  为了构建能够筛选寡糖-蛋白质相互作用的工具，我们开发了一种基于聚吡咯的寡糖芯片，它是通过吡咯和吡咯修饰寡糖的共聚过程构建而成的。在我们的研究中，参与许多基本生物过程的 GAG（糖胺聚糖）或 GAG 片段被吡咯分子修饰其还原端，然后固定在芯片上。通过表面等离子体共振成像（SPRi），可以同时实时监测和量化表面上侧的平行结合事件，而无需标记。我们的研究表明，在金表面上对低聚糖-吡咯进行电聚合，可以共价固定多个探针，然后利用表面等离子体共振成像技术监测它们的结合能力。此外，在生物应用中，不同的 GAG 片段和不同的蛋白质（包括基质细胞衍生因子-1α（SDF-1α）、干扰素-γ（IFN-γ）和单克隆抗体）显示出不同的亲和模式。