{2-[2-(7-Dimethylamino-2-oxo-2H-chromen-4-yl)-acetylamino]-ethyl}-carbamic acid tert-butyl ester | 861228-85-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: {2-[2-(7-Dimethylamino-2-oxo-2H-chromen-4-yl)-acetylamino]-ethyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-[[2-[7-(dimethylamino)-2-oxochromen-4-yl]acetyl]amino]ethyl]carbamate
• CAS: 861228-85-5
• 化学式: C₂₀H₂₇N₃O₅
• 分子量: 389.451
• InChiKey: MAZVLSJEZFYKCW-UHFFFAOYSA-N

物化性质

• 沸点：
  647.0±55.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  {2-[2-(7-Dimethylamino-2-oxo-2H-chromen-4-yl)-acetylamino]-ethyl}-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以98%的产率得到N-(2-Amino-ethyl)-2-(7-dimethylamino-2-oxo-2H-chromen-4-yl)-acetamide
  参考文献：
  名称：

  Paal–Knorr共轭对不可逆蛋白质的标记

  摘要：

  标记赖氨酸：一系列生物正交化学反应的最新进展极大地增强了生物化学家研究蛋白质和其他生物分子的工具。在这里，我们描述了使用Paal-Knorr反应来荧光标记蛋白质。根据生物相容性方法的需要，所描述的程序无需试剂，催化剂或有机溶剂即可运行。

  DOI：

  10.1002/cbic.201700210
• 作为产物：
  描述：

  N-叔丁氧羰基-1,2-乙二胺 、 7-二甲氨基香豆素-4-乙酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 以85%的产率得到{2-[2-(7-Dimethylamino-2-oxo-2H-chromen-4-yl)-acetylamino]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Fluorescent Profiling of Natural Product Producers

  摘要：

  The identification of natural product producer organisms remains a problem for both isolation and natural product classification. A concise screen is developed through fluorescent modification of a set of natural products that offer a common activity. Through real-time multicolor microscopy, the processing, storage, and effects of a natural product are rapidly screened at the level of the strain and individual organism.

  DOI：

  10.1021/ja042756u

文献信息

• PROBE FOR iFRET AND USE THEREOF
  申请人：Chung Sang Jeon

  公开号：US20140242606A1

  公开（公告）日：2014-08-28

  The present invention relates to a probe for iFRET and use thereof. Specifically, the present invention relates to a novel probe for iFRET, a method for preparing the probe for iFRET, a method for searching a target protein-specific binding site or a molecule having the binding site using the probe for iFRET, and a method for imaging the target protein using the probe for iFRET. The probe for iFRET according to the present invention utilizes an amino acid in a protein as a fluorescent donor, unlike the conventional FRET method. Therefore, only one fluorescent material is used, and its emission wavelength is distinct from the intrinsic fluorescence of the protein. Thus, high specificity and sensitivity are ensured, and the quantity, activity and mechanism of various proteins can be analyzed in an easy and accurate manner.

  本发明涉及一种用于iFRET的探针及其使用。具体而言，本发明涉及一种新型iFRET探针、制备iFRET探针的方法、使用iFRET探针搜索靶蛋白特异性结合位点或具有结合位点的分子的方法，以及使用iFRET探针成像靶蛋白的方法。本发明的iFRET探针利用蛋白质中的氨基酸作为荧光给体，而不是传统的FRET方法。因此，仅使用一个荧光材料，其发射波长与蛋白质的内在荧光不同。因此，确保了高度的特异性和灵敏度，并且可以轻松准确地分析各种蛋白质的数量、活性和机制。
• PROBE FOR IFRET AND USAGE OF SAME
  申请人：Korea Research Institute Of Bioscience And Biotechnology

  公开号：EP2725357A2

  公开（公告）日：2014-04-30

  The present invention relates to a probe for iFRET and use thereof. Specifically, the present invention relates to a novel probe for iFRET, a method for preparing the probe for iFRET, a method for searching a target protein-specific binding site or a molecule having the binding site using the probe for iFRET, and a method for imaging the target protein using the probe for iFRET. The probe for iFRET according to the present invention utilizes an amino acid in a protein as a fluorescent donor, unlike the conventional FRET method. Therefore, only one fluorescent material is used, and its emission wavelength is distinct from the intrinsic fluorescence of the protein. Thus, high specificity and sensitivity are ensured, and the quantity, activity and mechanism of various proteins can be analyzed in an easy and accurate manner.

  本发明涉及一种 iFRET 探针及其用途。具体而言，本发明涉及一种新型 iFRET 探针、一种制备 iFRET 探针的方法、一种使用 iFRET 探针搜索目标蛋白质特异性结合位点或具有该结合位点的分子的方法，以及一种使用 iFRET 探针对目标蛋白质成像的方法。与传统的 FRET 方法不同，本发明的 iFRET 用探针利用蛋白质中的一个氨基酸作为荧光供体。因此，只需使用一种荧光材料，其发射波长与蛋白质的固有荧光不同。因此，可确保高特异性和高灵敏度，并可轻松准确地分析各种蛋白质的数量、活性和机理。
• Fluorescent Profiling of Natural Product Producers
  作者：Joel S. Sandler、William Fenical、Brian M. Gulledge、A. Richard Chamberlin、James J. La Clair

  DOI：10.1021/ja042756u

  日期：2005.7.1

  The identification of natural product producer organisms remains a problem for both isolation and natural product classification. A concise screen is developed through fluorescent modification of a set of natural products that offer a common activity. Through real-time multicolor microscopy, the processing, storage, and effects of a natural product are rapidly screened at the level of the strain and individual organism.
• Examination of the Mode of Action of the Almiramide Family of Natural Products against the Kinetoplastid Parasite <i>Trypanosoma brucei</i>
  作者：Laura M. Sanchez、Giselle M. Knudsen、Claudia Helbig、Geraldine De Muylder、Samantha M. Mascuch、Zachary B. Mackey、Lena Gerwick、Christine Clayton、James H. McKerrow、Roger G. Linington

  DOI：10.1021/np300834q

  日期：2013.4.26

  Almiramide C is a marine natural product with low micromolar activity against Leishmania donovani, the causative agent of leishmaniasis. We have now shown that almiramide C is also active against the related parasite Ttypanosoma brucei, the causative agent of human African trypanosomiasis. A series of activity-based probes have been synthesized to explore both the molecular target of this compound series in T. brucei lysates and site localization through epifluorescence microscopy. These target identification studies indicate that the almiramides likely perturb glycosomal function through disruption of membrane assembly machinery. Glycosomes, which are organelles specific to kinetoplastid parasites, house the first seven steps of glycolysis and have been shown to be essential for parasite survival in the bloodstream stage. There are currently no reported smallmolecule disruptors of glycosome function, making the almiramides unique molecular probes for this understudied parasitespecific organelle. Additionally, examination of toxicity in an in vivo zebrafish model has shown that these compounds have little effect on organism development, even at high concentrations, and has uncovered a potential side effect through localization of fluorescent derivatives to zebrafish neuromast cells. Combined, these results further our understanding of the potential value of this lead series as development candidates against T. brucei.
• Irreversible Protein Labeling by Paal-Knorr Conjugation
  作者：Ramesh Dasari、James J. La Clair、Alexander Kornienko

  DOI：10.1002/cbic.201700210

  日期：2017.9.19

  lysines: Recent advances toward a suite of bioorthogonal chemical reactions have profoundly enhanced the tools available to biochemists to study proteins and other biomolecules. Here, we describe the use of the Paal–Knorr reaction to fluorescently label proteins. The described procedures operate without reagents, catalysts, or organic solvents, as needed for a biocompatible method.

  标记赖氨酸：一系列生物正交化学反应的最新进展极大地增强了生物化学家研究蛋白质和其他生物分子的工具。在这里，我们描述了使用Paal-Knorr反应来荧光标记蛋白质。根据生物相容性方法的需要，所描述的程序无需试剂，催化剂或有机溶剂即可运行。