5-azido-2-bromomethyl-8-tert-butyldiphenylsilyloxyquinoline | 1190595-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-azido-2-bromomethyl-8-tert-butyldiphenylsilyloxyquinoline
• 英文别名: 5-azido-2-bromomethyl-8-tert-butyldiphenysilyloxyquinoline；[5-Azido-2-(bromomethyl)quinolin-8-yl]oxy-tert-butyl-diphenylsilane
• CAS: 1190595-28-8
• 化学式: C₂₆H₂₅BrN₄OSi
• 分子量: 517.5
• InChiKey: ANFNZBAGSXIENM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.01
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  36.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-溴苯基)乙炔 、 5-azido-2-bromomethyl-8-tert-butyldiphenylsilyloxyquinoline 、 Fmoc-甘氨酸 、 Fmoc-L-丙氨酸 、 Fmoc-L-苯丙氨酸 、 Fmoc-O-叔丁基-L-谷氨酸 、 乙酸酐 、 Fmoc-L-异亮氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 N-芴甲氧羰基-O-苄基-L-磷酸酪氨酸 、 Fmoc-S-(4-甲氧基三苯甲基)-L-半胱氨酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 4-甲基哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 Ac-AEE-C(Clk)-IpYGEFEAKKKK-CONH2
  参考文献：
  名称：

  Synthesis of Red-Shifted 8-Hydroxyquinoline Derivatives Using Click Chemistry and Their Incorporation into Phosphorylation Chemosensors

  摘要：

  Protein phosphorylation is a ubiquitous post-translational modification, and protein kinases, the enzymes that catalyze the phosphoryl transfer, are involved in nearly every aspect of normal, as well as aberrant, cell function. Here we describe the synthesis of novel. red-shifted 8-hydroxyquinoline-based fluorophores and their incorporation into peptidyl kinase activity reporters. Replacement of the sulfonamide group of the sulfonamido-oxine (1, Sox) chromophore, which has been previously used In kinase sensing, by a 1,4-substituted triazole moiety prepared via click chemistry resulted in a significant bathochromic shift in the fluorescence excitation (15 nm) and emission (40 rim) maxima for the Mg2+ chelate. Furthermore, when a click derivative was incorporated into a chemosensor for MK2, the kinase accepted the new substrate as efficiently as the previously reported Sox-based sensor. Taken together, these results extend the utility range of kinase sensors that are based on chelation-enhanced fluorescence (CHEF).

  DOI：

  10.1021/jo901369k
• 作为产物：
  描述：

  5-azido-8-tert-butyldiphenylsilyloxy-2-methylquinoline 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 0.33h， 生成 5-azido-2-bromomethyl-8-tert-butyldiphenylsilyloxyquinoline
  参考文献：
  名称：

  [EN] 1, 2, 3-TRIAZOLE CONTAINING PROTEIN KINASE SENSORS
  [FR] 1, 2, 3-TRIAZOLE CONTENANT DES DÉTECTEURS DE PROTÉINE KINASE

  摘要：

  本发明通常涉及用于确定激酶活性的组合物和方法。在某些情况下，这些组合物包括三唑杂环。在某些实施例中，这些组合物包括喹啉基团。在一个方面，本发明涉及能够经历螯合增强荧光（CHEF）的组合物。在某些情况下，这些组合物可能具有峰值大于490纳米的荧光发射光谱。在某些实施例中，本发明的组合物可用于检测磷酸化底物和生物过程，如磷酸化事件。

  公开号：

  WO2011025546A1

文献信息

• [EN] 1, 2, 3-TRIAZOLE CONTAINING PROTEIN KINASE SENSORS<br/>[FR] 1, 2, 3-TRIAZOLE CONTENANT DES DÉTECTEURS DE PROTÉINE KINASE
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2011025546A1

  公开（公告）日：2011-03-03

  The present invention generally relates to compositions and methods for determining kinase activity. In some cases, the compositions comprise a triazole heterocycle. In some embodiments, the compositions comprise a quinoline moiety. In one aspect, the present invention is directed to compositions that undergo chelation- enhanced fluorescence (CHEF). In some cases, the compositions may have fluorescence emission spectra with peak maxima greater than 490 nm. The compositions of the present invention can be used, in certain embodiments, to detect phosphorylated substrates and biological processes such as phosphorylation events.

  本发明通常涉及用于确定激酶活性的组合物和方法。在某些情况下，这些组合物包括三唑杂环。在某些实施例中，这些组合物包括喹啉基团。在一个方面，本发明涉及能够经历螯合增强荧光（CHEF）的组合物。在某些情况下，这些组合物可能具有峰值大于490纳米的荧光发射光谱。在某些实施例中，本发明的组合物可用于检测磷酸化底物和生物过程，如磷酸化事件。
• Synthesis of Red-Shifted 8-Hydroxyquinoline Derivatives Using Click Chemistry and Their Incorporation into Phosphorylation Chemosensors
  作者：Juan A. González-Vera、Elvedin Luković、Barbara Imperiali

  DOI：10.1021/jo901369k

  日期：2009.10.2

  Protein phosphorylation is a ubiquitous post-translational modification, and protein kinases, the enzymes that catalyze the phosphoryl transfer, are involved in nearly every aspect of normal, as well as aberrant, cell function. Here we describe the synthesis of novel. red-shifted 8-hydroxyquinoline-based fluorophores and their incorporation into peptidyl kinase activity reporters. Replacement of the sulfonamide group of the sulfonamido-oxine (1, Sox) chromophore, which has been previously used In kinase sensing, by a 1,4-substituted triazole moiety prepared via click chemistry resulted in a significant bathochromic shift in the fluorescence excitation (15 nm) and emission (40 rim) maxima for the Mg2+ chelate. Furthermore, when a click derivative was incorporated into a chemosensor for MK2, the kinase accepted the new substrate as efficiently as the previously reported Sox-based sensor. Taken together, these results extend the utility range of kinase sensors that are based on chelation-enhanced fluorescence (CHEF).