toluene-4-sulfonic acid 2-{2-[2-(2-N,N-bis(tert-butoxycarbonyl)aminoethoxy)ethoxy]ethoxy}ethyl ester | 688025-28-7

• 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: toluene-4-sulfonic acid 2-{2-[2-(2-N,N-bis(tert-butoxycarbonyl)aminoethoxy)ethoxy]ethoxy}ethyl ester
• 英文别名: 2-[2-[2-[2-(4-methylphenylsulfonyloxo)ethoxy]ethoxy]ethoxy]ethyl di(tert)butyliminocarboxylate；2-[2-[2-[2-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]ethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate
• CAS: 688025-28-7
• 化学式: C₂₅H₄₁NO₁₀S
• 分子量: 547.667
• InChiKey: MDNJJCNASHDAFC-UHFFFAOYSA-N

物化性质

• 沸点：
  604.2±65.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  37.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  126.9
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  toluene-4-sulfonic acid 2-{2-[2-(2-N,N-bis(tert-butoxycarbonyl)aminoethoxy)ethoxy]ethoxy}ethyl ester 在 三氟乙酸 、 potassium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  基于尼罗红的 GPCR 配体作为受体局部脂质微环境的超灵敏探针

  摘要：

  跨膜受体的局部脂质微环境是 G 蛋白偶联受体 (GPCR) 信号传导的重要因素。然而，目前缺少用于研究原代细胞和组织中内源性表达的 GPCR 的工具。在这里，我们引入了荧光环境敏感 GPCR 配体，用于在无洗涤条件下使用荧光显微镜探测活细胞中受体的微环境。我们通过将高亲和力非肽 OTR 配体 PF-3274167 与环境敏感荧光染料尼罗红结合，设计并合成了催产素受体 (OTR) 的拮抗剂配体。调整药效团和荧光团之间的极性 PEG 间隔物的长度以降低探针的非特异性相互作用，同时保持强烈的荧光反应。

  DOI：

  10.1021/acschembio.0c00897
• 作为产物：
  描述：

  四乙二醇二对甲苯磺酸酯 、 双(叔丁氧羰基)胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以39%的产率得到toluene-4-sulfonic acid 2-{2-[2-(2-N,N-bis(tert-butoxycarbonyl)aminoethoxy)ethoxy]ethoxy}ethyl ester
  参考文献：
  名称：

  Synthesis of AX7593, a Quinazoline-Derived Photoaffinity Probe for EGFR

  摘要：

  The synthesis of a photoaffinity probe for EGFR is described. O-Alkylation of 4-(meta-azidoanllino)-6-methoxy-7-hydroxy-quinazoline with a protected tetraethyleneglycol linker followed by the attachment of tetramethylrhodamine yielded the fluorescent probe AX7593. Photoaffinity labeling of EGFR by AX7593 (K-b = 280 nM) was shown to have an efficiency of 34% and to be competitive with the EGFR inhibitors PP2 and AG1478.

  DOI：

  10.1021/ol048656a

文献信息

• Affinity electrophoresis in multisectional polyacrylamide slab gels is a useful and convenient technique for measuring binding constants of aryl sulfonamides to bovine carbonic anhydrase B
  作者：Yen Ho. Chu、James K. Chen、George M. Whitesides

  DOI：10.1021/ac00058a004

  日期：1993.5.15

  This paper describes convenient preparations of heterogeneous multisectional polyacrylamide slab gels and the protocols that use these gels to measure protein-ligand binding constants [using bovine carbonic anhydrase B (CAB) as a model system]. Unlike procedures for affinity electrophoresis using tube gels, all binding information concerning protein-ligand interactions was encoded in a single multisectional gel: the procedure involving for measuring binding constants required no postelectrophoresis manipulation of gels. Use of these types of gels improves the accuracy of affinity gel electrophoresis (AGE) by providing reliable internal protein standards. Binding constants measured by AGE agree with those determined in homogeneous solution by spectrophotometric measurements. This technique has been used to investigate the influence of the length of the spacer separating the ligand and the polyacrylamide backbone on the binding constants. Dissociation constants obtained using the affinity gels approach the values measured in free solution, when the spacer is sufficiently long (greater-than-or-equal-to 18 angstrom); affinity ligands having short spacers give high apparent dissociation constants.
• Selective Nonpeptidic Fluorescent Ligands for Oxytocin Receptor: Design, Synthesis, and Application to Time-Resolved FRET Binding Assay
  作者：Iuliia A. Karpenko、Jean-François Margathe、Thiéric Rodriguez、Elsa Pflimlin、Elodie Dupuis、Marcel Hibert、Thierry Durroux、Dominique Bonnet

  DOI：10.1021/jm501395b

  日期：2015.3.12

  The design and the synthesis of the first high-affinity fluorescent ligands for oxytocin receptor (OTR) are described. These compounds enabled the development of a TR-FRET based assay for OTR, readily amenable to high throughput screening. The validation of the assay was achieved by competition experiments with both peptide and nonpeptide OTR ligands as competitors. These probes represent the first selective fluorescent ligands for the oxytocin G protein-coupled receptor.