11-(pyrrol-1-yl)-undecanoic acid | 137025-07-1

• 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: 11-(pyrrol-1-yl)-undecanoic acid
• 英文别名: 3-(pyrrol-1-yl)undecanoic acid；1-(11-carboxyundecyl)pyrrole；11-Pyrrol-1-yl-undecanoic acid；11-pyrrol-1-ylundecanoic acid
• CAS: 137025-07-1
• 化学式: C₁₅H₂₅NO₂
• 分子量: 251.369
• InChiKey: RCBJPUNFMOQCAC-UHFFFAOYSA-N

物化性质

• 熔点：
  36-37 °C(Solv: heptane (142-82-5))
• 沸点：
  398.6±15.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11-(pyrrol-1-yl)-undecanoic acid 在 sodium hydroxide 、 TEA 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成
  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
• 作为产物：
  描述：

  1,10-二溴癸烷 在 氢氧化钾 、 水 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 0.17h， 生成 11-(pyrrol-1-yl)-undecanoic acid
  参考文献：
  名称：

  Functionalization of polypyrroles with acids and β-diketones as complexing groups. Part 1: electrochemical synthesis and properties

  摘要：

  文中描述了通过乙酰丙酮、二苯甲酰甲烷或羧酸等配位基团功能化的吡咯的合成方法，以及它们电氧化成为功能化聚吡咯的过程。我们通过循环伏安法(CV)和红外(IR)光谱研究了聚(功能化吡咯)薄膜在Li+、Ni2+和Co2+阳离子存在下的行为。在不同条件下，电化学响应随配位基团性质的不同而有所差异。我们还展示了通过电化学方法生成吡咯和每种功能化吡咯的共聚物的可能性。通过跟踪循环伏安法中峰电位的依赖性来估计共聚物中功能基团的比例，并通过红外光谱确认。

  DOI：

  10.1039/b002460k

文献信息

• 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。
• Method for fixing a protein on a pyrrole-based polymer and use thereof for making a sensor
  申请人：Roget Andre

  公开号：US20060035208A1

  公开（公告）日：2006-02-16

  The aim of the present invention is to provide a method for attaching a protein to a conductive polymer, that can be used in particular for producing a sensor or a multisensor, for example a biochip. This aim, and also others, are achieved, in accordance with the invention, by means of a method for attaching a protein to a pyrrole polymer, comprising the following steps: coupling of the protein to be attached with pyrrole so as to obtain a first solution of a protein-pyrrole coupling compound, preparation of a second solution of pyrrole not containing the protein, mixing of said first solution with said second solution so as to obtain an electropolymerization solution, electropolymerization of the pyrrole and of the protein coupled to the pyrrole on a conductive support using said electropolymerization solution.

  本发明的目的是提供一种将蛋白质附着在导电聚合物上的方法，特别适用于生产传感器或多传感器，例如生物芯片。根据本发明，通过以下步骤实现了该目的以及其他目的：将待附着的蛋白质与吡咯偶联以获得蛋白质-吡咯偶联化合物的第一溶液，制备不含蛋白质的吡咯的第二溶液，将第一溶液与第二溶液混合以获得电聚合溶液，在导电支撑物上使用所述电聚合溶液对吡咯和与吡咯偶联的蛋白质进行电聚合。
• US7998726B2
  申请人：——

  公开号：US7998726B2

  公开（公告）日：2011-08-16
• Functionalization of polypyrroles with acids and β-diketones as complexing groups. Part 1: electrochemical synthesis and properties
  作者：Ste´phane Roux、Pierre Audebert、Jacques Pagetti、Maxime Roche

  DOI：10.1039/b002460k

  日期：——

  The synthesis of pyrroles functionalized by complexing groups such as acetylacetone, dibenzoylmethane or carboxylic acids is described, as well as their electrooxidation into functionalized polypyrroles. We have studied the behavior of poly(functionalized pyrrole) films in the presence of Li+, Ni2+ and Co2+ cations by cyclic voltammetry (CV) and infrared (IR) spectroscopy. The electrochemical response under various conditions differs with the nature of the complexing group. We have also demonstrated the possibility to electrochemically generate copolymers with pyrrole and each functionalized pyrrole. The proportion of functional groups in the copolymers was estimated by following the peak potential dependence in cyclic voltammetry and was confirmed by IR spectroscopy.

  文中描述了通过乙酰丙酮、二苯甲酰甲烷或羧酸等配位基团功能化的吡咯的合成方法，以及它们电氧化成为功能化聚吡咯的过程。我们通过循环伏安法(CV)和红外(IR)光谱研究了聚(功能化吡咯)薄膜在Li+、Ni2+和Co2+阳离子存在下的行为。在不同条件下，电化学响应随配位基团性质的不同而有所差异。我们还展示了通过电化学方法生成吡咯和每种功能化吡咯的共聚物的可能性。通过跟踪循环伏安法中峰电位的依赖性来估计共聚物中功能基团的比例，并通过红外光谱确认。
• 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.