[11-(2,5-Dioxo-pyrrolidin-1-yloxycarbonyloxy)-undecyl]-phosphonic acid 12-(7-nitro-benzo[1,2,5]oxadiazol-4-ylamino)-dodecyl ester 4-nitro-phenyl ester | 935553-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: [11-(2,5-Dioxo-pyrrolidin-1-yloxycarbonyloxy)-undecyl]-phosphonic acid 12-(7-nitro-benzo[1,2,5]oxadiazol-4-ylamino)-dodecyl ester 4-nitro-phenyl ester
• CAS: 935553-25-6
• 化学式: C₄₀H₅₇N₆O₁₃P
• 分子量: 860.899
• InChiKey: XZVFYLSKMVEOAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.37
• 重原子数：
  60.0
• 可旋转键数：
  32.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  245.67
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  N-(6-aminohexyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide triflouroacetate 、 [11-(2,5-Dioxo-pyrrolidin-1-yloxycarbonyloxy)-undecyl]-phosphonic acid 12-(7-nitro-benzo[1,2,5]oxadiazol-4-ylamino)-dodecyl ester 4-nitro-phenyl ester 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以37%的产率得到(11-{6-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexylcarbamoyloxy}-undecyl)-phosphonic acid 12-(7-nitro-benzo[1,2,5]oxadiazol-4-ylamino)-dodecyl ester 4-nitro-phenyl ester
  参考文献：
  名称：

  A versatile library of activity-based probes for fluorescence detection and/or affinity isolation of lipolytic enzymes

  摘要：

  This work describes the synthesis of a library of fluorescent and/or biotinylated alkylphosphonate inhibitors being reactive towards serine hydrolases, especially lipases and esterases. Fluorescent inhibitors can be used for sensitive and rapid detection of active proteins by gel electrophoresis. Biotinylated inhibitors are applicable for the enrichment and isolation of active enzymes. Functionality as well as the different detection methods of the synthesized inhibitors were successfully tested with an enzyme preparation, namely cholesterol esterase from porcine pancreas (ppCE). Moreover, a biotinylated inhibitor was employed to enrich ppCE on avidin beads. Hence, our set of phosphonate inhibitors can be used for the detection and/or isolation of active serine hydrolases. (c) 2006 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2006.06.018
• 作为产物：
  描述：

  ethyl (4-nitrophenyl)[11-([(2,5-dioxotetrahydro-1H-1-pyrrolyl)oxy]carbonyloxy)undecyl]phosphonate 在 草酰氯 、 三甲基溴硅烷 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 66.0h， 生成 [11-(2,5-Dioxo-pyrrolidin-1-yloxycarbonyloxy)-undecyl]-phosphonic acid 12-(7-nitro-benzo[1,2,5]oxadiazol-4-ylamino)-dodecyl ester 4-nitro-phenyl ester
  参考文献：
  名称：

  A versatile library of activity-based probes for fluorescence detection and/or affinity isolation of lipolytic enzymes

  摘要：

  This work describes the synthesis of a library of fluorescent and/or biotinylated alkylphosphonate inhibitors being reactive towards serine hydrolases, especially lipases and esterases. Fluorescent inhibitors can be used for sensitive and rapid detection of active proteins by gel electrophoresis. Biotinylated inhibitors are applicable for the enrichment and isolation of active enzymes. Functionality as well as the different detection methods of the synthesized inhibitors were successfully tested with an enzyme preparation, namely cholesterol esterase from porcine pancreas (ppCE). Moreover, a biotinylated inhibitor was employed to enrich ppCE on avidin beads. Hence, our set of phosphonate inhibitors can be used for the detection and/or isolation of active serine hydrolases. (c) 2006 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2006.06.018