tert-Butyl 5-(3-(chlorosulfonyl)benzamido)pentylcarbamate | 1158798-38-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-Butyl 5-(3-(chlorosulfonyl)benzamido)pentylcarbamate
• 英文别名: tert-butyl N-[5-[(3-chlorosulfonylbenzoyl)amino]pentyl]carbamate
• CAS: 1158798-38-9
• 化学式: C₁₇H₂₅ClN₂O₅S
• 分子量: 404.915
• InChiKey: IDARKEWEBHIRSP-UHFFFAOYSA-N

物化性质

• 沸点：
  574.5±35.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-Butyl 5-(3-(chlorosulfonyl)benzamido)pentylcarbamate 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  JP5676853

  摘要：

  公开号：
• 作为产物：
  描述：

  3-氯磺酰苯甲酰氯 、 N-(5-氨基戊基)氨基甲酸叔丁酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以83%的产率得到tert-Butyl 5-(3-(chlorosulfonyl)benzamido)pentylcarbamate
  参考文献：
  名称：

  Native FKBP12 Engineering by Ligand-Directed Tosyl Chemistry: Labeling Properties and Application to Photo-Cross-Linking of Protein Complexes in Vitro and in Living Cells

  摘要：

  The ability to modify target "native" (endogenous) proteins selectively in living cells with synthetic molecules should provide powerful tools for chemical biology. To this end, we recently developed a novel protein labeling technique termed ligand-directed tosyl (LDT) chemistry. This method uses labeling reagents in which a protein ligand and a synthetic probe are connected by a tosylate ester group. We previously demonstrated its applicability to the selective chemical labeling of several native proteins in living cells and mice. However, many fundamental features of this chemistry remain to be studied. In this work, we investigated the relationship between the LDT reagent structure and labeling properties by using native FK506-binding protein 12 (FKBP12) as a target protein. In vitro experiments revealed that the length and rigidity of the spacer structure linking the protein ligand and the tosylate group have significant effects on the overall labeling yield and labeling site. In addition to histidine, which we reported previously, tyrosine and glutamate residues were identified as amino acids that are modified by LDT-mediated labeling. Through the screening of various spacer structures, piperazine was found to be optimal for FKBP12 labeling in terms of labeling efficiency and site specificity. Using a piperazine-based LDT reagent containing a photoreactive probe, we successfully demonstrated the labeling and UV-induced covalent cross-linking of FKBP12 and its interacting proteins in vitro and in living cells. This study not only furthers our understanding of the basic reaction properties of LDT chemistry but also extends the applicability of this method to the investigation of biological processes in mammalian cells.

  DOI：

  10.1021/ja209641t

文献信息

• Live‐Cell Protein Sulfonylation Based on Proximity‐driven <i>N</i> ‐Sulfonyl Pyridone Chemistry
  作者：Kazuya Matsuo、Yuki Nishikawa、Marie Masuda、Itaru Hamachi

  DOI：10.1002/anie.201707972

  日期：2018.1.15

  multimolecular crowding conditions of live cells is highly desirable for the analysis and engineering of proteins without using genetic manipulation. N‐Sulfonyl pyridone (SP) is reported as a new reactive group for protein sulfonylation. The ligand‐directed SP chemistry was able to modify not only purified proteins in vitro, but also endogenous ones on the surface of and inside live cells selectively and rapidly

  在不使用基因操作的情况下，非常需要开发用于在活细胞多分子拥挤条件下标记内源蛋白的生物正交方法。据报道，N-磺酰基吡啶酮（SP）是蛋白质磺酰化的一个新的反应基团。配体导向的SP化学不仅能够在体外修饰纯化的蛋白质，而且能够选择性且快速地修饰活细胞表面和内部的内源性蛋白质，从而可以将内源性蛋白质原位转化为基于FRET的生物传感器。
• Systematic Study of Protein Detection Mechanism of Self-Assembling ¹⁹F NMR/MRI Nanoprobes toward Rational Design and Improved Sensitivity
  作者：Yousuke Takaoka、Keishi Kiminami、Keigo Mizusawa、Kazuya Matsuo、Michiko Narazaki、Tetsuya Matsuda、Itaru Hamachi

  DOI：10.1021/ja203996c

  日期：2011.8.3

  nanoprobes, which induced a clear turn-on signal of (19)F NMR/MRI. In the present study, we conducted a systematic investigation of the relationship between structure and properties of the probe to elucidate the mechanism of this turn-on (19)F NMR sensing in detail. Newly synthesized (19)F probes showed three distinct behaviors in response to the target protein: off/on, always-on, and always-off modes. We

  (19)F NMR/MRI 探针由于其高灵敏度且在活体中没有背景信号，因此有望成为选择性传感生物活性剂的有力工具。我们最近报道了一种使用蛋白质配体束缚自组装 (19) F 探针检测特定蛋白质的独特超分子策略。该方法基于纳米探针的识别驱动拆卸，其诱导了 (19)F NMR/MRI 的清晰开启信号。在本研究中，我们对探针的结构和性质之间的关系进行了系统研究，以详细阐明这种开启（19）F NMR 传感的机制。新合成的 (19) F 探针在响应目标蛋白时表现出三种不同的行为：关闭/开启、始终开启和始终关闭模式。我们清楚地证明了蛋白质反应的这些差异可以用探针聚集体稳定性的差异来解释，并且聚集体的“中等稳定性”在蛋白质检测中产生了理想的开启响应。我们还通过改变探针的疏水性/亲水性平衡成功地控制了聚合稳定性。对检测机制的详细理解使我们能够合理设计具有更高灵敏度的开启（19）F NMR 探针，为（19）F
• Disassembly-Driven Turn-On Fluorescent Nanoprobes for Selective Protein Detection
  作者：Keigo Mizusawa、Yoshiyuki Ishida、Yousuke Takaoka、Masayoshi Miyagawa、Shinya Tsukiji、Itaru Hamachi

  DOI：10.1021/ja101879g

  日期：2010.6.2

  "Switchable" fluorescent probes, which induce changes in the fluorescence properties (e.g., intensity and/or wavelength) only at the intended target protein, are particularly useful for selective protein detection or imaging. However, the strategy for designing such smart probes remains very limited. We report herein a novel mechanism for generating protein-specific "turn-on" fluorescent probes. Our approach uses an amphiphilic, self-assembling compound consisting of a fluorophore and a protein ligand. In the absence of target protein, the probe forms self-assembled aggregates in aqueous solution and displays almost no fluorescence because of efficient quenching. On the other hand, it emits bright fluorescence in response to the target protein through recognition-induced disassembly of the probe. On the basis of this strategy, we successfully developed three types of fluorescent probes that allow the detection of carbonic anhydrase, avidin, and trypsin via turn-on emission signals. It is anticipated that the present supramolecular approach may facilitate the development of new protein-specific switchable fluorescent probes that are useful for a wide range of applications, such as diagnosis and molecular imaging.

  具有“可切换型”荧光探针，其仅在目标蛋白位置诱导荧光特性（如强度和/或波长）发生变化，特别适用于选择性检测或成像蛋白质。然而，设计此类智能探针的策略仍然非常有限。本文中，我们报告了一种生成特异性蛋白“开启”荧光探针的新机制。我们的方法使用了一种由荧光团和蛋白配体组成的两亲性、自组装化合物。在没有目标蛋白的情况下，探针在水溶液中形成自组装聚集体，由于有效的淬灭作用，几乎不显示荧光。另一方面，它通过识别诱导的探针解组装对目标蛋白产生明亮的荧光。基于此策略，我们成功开发了三种类型的荧光探针，它们允许通过“开启”发射信号检测碳酸酐酶、链霉抗生物素蛋白和胰蛋白酶。预计目前的超分子方法可能有助于开发新的特异性蛋白可切换型荧光探针，可用于多种应用，如诊断和分子成像。 - **详细说明**： - **术语一致性**：确保所有专业术语（如“fluorescence probes”、“amphiphilic”、“self-assembling”等）在中文中有准确对应的翻译，并保持一致性。 - **准确性**： - “carbonic anhydrase”译为“碳酸酐酶”。 - “avidin”译为“链霉抗生物素蛋白”。 - “trypsin”译为“胰蛋白酶”。 - **句子流畅性**： - 将英文中的长句拆分为更易于理解的中文短句，例如将英文的复合句转化为多个衔接自然的中文句子。 - 使用常见的连接词（如“然而”、“同时”、“因此”等）以增强逻辑性和连贯性。
• Specific Cell Surface Protein Imaging by Extended Self-Assembling Fluorescent Turn-on Nanoprobes
  作者：Keigo Mizusawa、Yousuke Takaoka、Itaru Hamachi

  DOI：10.1021/ja304239g

  日期：2012.8.15

  Visualization of tumor-specific protein biomarkers on cell membranes has the potential to contribute greatly to basic biological research and therapeutic applications. We recently reported a unique supramolecular strategy for specific protein detection using self-assembling fluorescent nanoprobes consisting of a hydrophilic protein ligand and a hydrophobic BODIPY fluorophore in test tube settings. This method is based on recognition-driven disassembly of the nanoprobes, which induces a clear turn-on fluorescent signal. In the present study, we have successfully extended the range of applicable fluorophores to the more hydrophilic ones such as fluorescein or rhodamine by introducing a hydrophobic module near the fluorophore. Increasing the range of available fluorophores allowed selective imaging of membrane-bound proteins under live cell conditions. That is, overexpressed folate receptor (FR) or hypoxia-inducible membrane-bound carbonic anhydrases (CA) on live cell surfaces as cancer-specific biomarkers were fluorescently visualized using the designed supramolecular nanoprobes in the turn-on manner. Moreover, a cell-based inhibitor-assay platform for CA on a live cell surface was constructed, highlighting the potential applicability of the self-assembling turn-on probes.
• [EN] FLUORINE-CONTAINING COMPOUND AND METHOD FOR DETECTING BIOMOLECULE USING THE SAME<br/>[FR] COMPOSÉ CONTENANT DU FLUOR ET PROCÉDÉ DE DÉTECTION DE BIOMPLÉCULE L'UTILISANT
  申请人：UNIV KYOTO

  公开号：WO2009113704A2

  公开（公告）日：2009-09-17

  The present invention provides an amphiphilic fluorine-containing compound having a structure represented by the following general formula (1) including a hydrophilic ligand Rl, a fluorine probe Rf, and linkers L1 and L2. In the formula, Rl is a hydrophilic ligand having a polar group; L2 is an alkylene group having one or more -CH2- which may independently be substituted by one of -NH-, -O-, -CO-, -SO2-, and an arylene group; Rf is selected from an alkyl group having one or more hydrogen atoms substituted by a fluorine atom and from an aryl group having at least one hydrogen atom substituted by one of F and a perfluoroalkyl group; m is selected from 0 and 1; and n is selected from 0 and 1. An aggregate including the compounds is destabilized through the binding to an enzyme. (1)