Ac-AEE-C(Clk)-IpYGEFEAKKKK-CONH2 | 1190595-30-2

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: Ac-AEE-C(Clk)-IpYGEFEAKKKK-CONH2
• 英文别名: (4S)-4-[[2-[[(2S)-2-[[(2S,3S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamidopropanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-[[5-[4-(4-bromophenyl)triazol-1-yl]-8-hydroxyquinolin-2-yl]methylsulfanyl]propanoyl]amino]-3-methylpentanoyl]amino]-3-(4-phosphonooxyphenyl)propanoyl]amino]acetyl]amino]-5-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-1,6-diamino-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-5-oxopentanoic acid
• CAS: 1190595-30-2
• 化学式: C₉₉H₁₄₀BrN₂₄O₂₉PS
• 分子量: 2273.29
• InChiKey: YRLYGQKZBUTLCQ-XPOGJLQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10.8
• 重原子数：
  155
• 可旋转键数：
  72
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  889
• 氢给体数：
  27
• 氢受体数：
  37

反应信息

• 作为产物：
  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

文献信息

• 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).