N^α-(4-(1-azi-2,2,2-trifluoroethyl)benzoyl)-L-biocytin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: N^α-(4-(1-azi-2,2,2-trifluoroethyl)benzoyl)-L-biocytin
• 英文别名: (2S)-6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-2-[[4-[3-(trifluoromethyl)diazirin-3-yl]benzoyl]amino]hexanoic acid
• 化学式: C₂₅H₃₁F₃N₆O₅S
• 分子量: 584.62
• InChiKey: YXNXAJWGKCYVMJ-JPLJXNOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  187
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  4-[3-(三氟甲基)二氮杂环丙烯-3-基]苯甲酸 N-羟基琥珀酰亚胺酯 、 生物胞素 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以91%的产率得到N^α-(4-(1-azi-2,2,2-trifluoroethyl)benzoyl)-L-biocytin
  参考文献：
  名称：

  Modular Design of Biotinylated Photoaffinity Probes: Synthesis and Utilization of a Biotinylated Pepstatin Photoprobe

  摘要：

  A novel modular design is presented for the introduction of biotinylated photoprobes containing either 4-azidotetrafluorobenzamide, 4-(1-azi-2,2,2-trifluoroethyl)benzamide, or 4-benzoylbenzoylamide. The use of biotinylated affinity labels offers several advantages over radiolabeled probes by virtue of their exploitation of the biotin-avidin system of detection and purification. A biotinylated benzoylbenzoyl photoprobe of pepstatin (BBB-pepstatin, 5) was synthesized in three steps from pepstatin. The photoprobe is a competitive inhibitor of porcine pepsin, with an apparent dissociation constant of 31 pM. Western blotting of BBB-pepstatin-photolabeled porcine pepsin, renin, cathepsin D and human renin, and cathepsin D could be detected with an avidin-horseradish peroxidase label. Routinely, 7 pM of aspartic protease could be photolabeled and detected with this system. The pepstatin photoaffinity probe is also very selective; the probe failed to label cysteine protease (papain), metalloprotease (carboxypepitase A), and serine protease (chymotrypsin and trypsin). To further establish the utility of the biotinylated probe, BBB-pepstain-photolabeled porcine pepsin was purified by monomeric avidin chromatography. This probe should be useful for the identification of unknown cytosolic and membrane-bound aspartic proteases.

  DOI：

  10.1021/ja00136a002

文献信息

• Capture compounds, collections thereof and methods for analyzing the proteome and complex compositions
  申请人：Kõster Hubert

  公开号：US20100248264A1

  公开（公告）日：2010-09-30

  Capture compounds and collections thereof and methods using the compounds for the analysis of biomolecules are provided. In particular, collections, compounds and methods are provided for analyzing complex protein mixtures, such as the proteome. The compounds are multifunctional reagents that provide for the separation and isolation of complex protein mixtures. Automated systems for performing the methods also are provided.

  提供了捕获化合物及其集合以及使用这些化合物进行生物分子分析的方法。特别地，提供了用于分析复杂蛋白质混合物（如蛋白质组）的集合、化合物和方法。这些化合物是多功能试剂，可用于分离和分离复杂的蛋白质混合物。还提供了执行这些方法的自动化系统。
• Capture compounds and methods for analyzing the proteome
  申请人：caprotec bioanalytics GmbH

  公开号：EP2259068B1

  公开（公告）日：2013-08-14
• US9034798B2
  申请人：——

  公开号：US9034798B2

  公开（公告）日：2015-05-19
• Modular Design of Biotinylated Photoaffinity Probes: Synthesis and Utilization of a Biotinylated Pepstatin Photoprobe
  作者：Bryant A. Gilbert、Robert R. Rando

  DOI：10.1021/ja00136a002

  日期：1995.8

  A novel modular design is presented for the introduction of biotinylated photoprobes containing either 4-azidotetrafluorobenzamide, 4-(1-azi-2,2,2-trifluoroethyl)benzamide, or 4-benzoylbenzoylamide. The use of biotinylated affinity labels offers several advantages over radiolabeled probes by virtue of their exploitation of the biotin-avidin system of detection and purification. A biotinylated benzoylbenzoyl photoprobe of pepstatin (BBB-pepstatin, 5) was synthesized in three steps from pepstatin. The photoprobe is a competitive inhibitor of porcine pepsin, with an apparent dissociation constant of 31 pM. Western blotting of BBB-pepstatin-photolabeled porcine pepsin, renin, cathepsin D and human renin, and cathepsin D could be detected with an avidin-horseradish peroxidase label. Routinely, 7 pM of aspartic protease could be photolabeled and detected with this system. The pepstatin photoaffinity probe is also very selective; the probe failed to label cysteine protease (papain), metalloprotease (carboxypepitase A), and serine protease (chymotrypsin and trypsin). To further establish the utility of the biotinylated probe, BBB-pepstain-photolabeled porcine pepsin was purified by monomeric avidin chromatography. This probe should be useful for the identification of unknown cytosolic and membrane-bound aspartic proteases.