ethyl (4-nitrophenyl)[11-([(2,5-dioxotetrahydro-1H-1-pyrrolyl)oxy]carbonyloxy)undecyl]phosphonate | 268227-43-6

• 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: ethyl (4-nitrophenyl)[11-([(2,5-dioxotetrahydro-1H-1-pyrrolyl)oxy]carbonyloxy)undecyl]phosphonate
• 英文别名: (2,5-Dioxopyrrolidin-1-yl) 11-[ethoxy-(4-nitrophenoxy)-oxidophosphaniumyl]undecyl carbonate；(2,5-dioxopyrrolidin-1-yl) 11-[ethoxy-(4-nitrophenoxy)-oxidophosphaniumyl]undecyl carbonate
• CAS: 268227-43-6
• 化学式: C₂₄H₃₅N₂O₁₀P
• 分子量: 542.523
• InChiKey: ZFXKJWQBYNTZBX-UHFFFAOYSA-N

物化性质

• 沸点：
  633.2±65.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  37
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  160
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  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 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：

  11-溴-1-十一醇 在 N-甲基吡咯烷酮 、 草酰氯 、 Amberlite IR-120 、 sodium hydride 、 对甲苯磺酸 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 16.0h， 生成 ethyl (4-nitrophenyl)[11-([(2,5-dioxotetrahydro-1H-1-pyrrolyl)oxy]carbonyloxy)undecyl]phosphonate
  参考文献：
  名称：

  Immobilization of chiral enzyme inhibitors on solid supports by amide-forming coupling and olefin metathesis

  摘要：

  The question whether phage display can be used as a selection method in the directed evolution of enantioselective enzymes has not been answered satisfactorily to date. In order to be able to test this in a specific case, namely in the hydrolytic kinetic resolution of the acetate derived from alpha,beta- isopropylideneglycerol (IPG) catalyzed by the lipase from Bacillus subtilis, suicide enzyme inhibitors anchored on porous glass or polymer beads were designed and synthesized. These are immobilized phosphonates, which bear a leaving group and also contain the chiral substrate (D) and (L)-IPG, Modified SIRAN((R)) (porous glass) and Tentagel((R)) (polymer) were chosen as carriers, attachment occurring via amide-forming coupling or Ru-catalyzed olefin metathesis. Initial lipase inhibition studies are also reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01052-9

文献信息

• A novel biotinylated suicide inhibitor for directed molecular evolution of lipolytic enzymes
  作者：H.-J. Deussen、S. Danielsen、J. Breinholt、T.V. Borchert

  DOI：10.1016/s0968-0896(00)00002-x

  日期：2000.3

  A bifunctional activity label (8) for directed molecular evolution of lipolytic enzymes has been designed and synthesized. The structure is composed of a 4-nitrophenyl activated phosphonate, that is, a suicide substrate of lipases/esterases, connected to a biotin moiety through a spacer containing a disulfide bridge. The phosphonate (3) was prepared by Michaelis-Arbuzov reaction of trimethylsilyl-protected 11-bromoundecanol (2) with triethyl phosphite. The deprotected omega-hydroxyalkylphosphonate (4) was transformed into an active N-hydroxysuccinimide carbonate (5) followed by 4-nitrophenyl activation of the phosphonate using standard procedures. The biotinylated phosphonate inhibitor (8) was then synthesised by coupling the phosphonate inhibitor (6) to the E-amino-caproic acid and cystamine containing biotinyl spacer (7). The function of all relevant groups of the final activity label (8) (biotin-label, cleavable disulfide bridge, phosphonate-inhibitor) have been successfully tested with the commercial lipase Lipolase(R) (Novo Nordisk). Hence, a tool for directed molecular evolution of lipolytic enzymes has been developed. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Design and synthesis of triglyceride analogue biotinylated suicide inhibitors for directed molecular evolution of lipolytic enzymes
  作者：H.-J Deussen、S Danielsen、J Breinholt、T.V Borchert

  DOI：10.1016/s0960-894x(00)00396-6

  日期：2000.9

  The design, Synthesis, and inhibition properties of two new triglyceride analogue biotinylated suicide inhibitors (2) and (3) for directed molecular evolution of lipolytic enzymes by phage-display is described. (C) 2000 Elsevier Science Ltd. All rights reserved.
• A versatile library of activity-based probes for fluorescence detection and/or affinity isolation of lipolytic enzymes
  作者：Heidrun Susani-Etzerodt、Hannes Schmidinger、Gernot Riesenhuber、Ruth Birner-Gruenberger、Albin Hermetter

  DOI：10.1016/j.chemphyslip.2006.06.018

  日期：2006.10

  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.
• Immobilization of chiral enzyme inhibitors on solid supports by amide-forming coupling and olefin metathesis
  作者：Manfred T Reetz、Carsten J Rüggeberg、Melloney J Dröge、Wim J Quax

  DOI：10.1016/s0040-4020(02)01052-9

  日期：2002.10

  The question whether phage display can be used as a selection method in the directed evolution of enantioselective enzymes has not been answered satisfactorily to date. In order to be able to test this in a specific case, namely in the hydrolytic kinetic resolution of the acetate derived from alpha,beta- isopropylideneglycerol (IPG) catalyzed by the lipase from Bacillus subtilis, suicide enzyme inhibitors anchored on porous glass or polymer beads were designed and synthesized. These are immobilized phosphonates, which bear a leaving group and also contain the chiral substrate (D) and (L)-IPG, Modified SIRAN((R)) (porous glass) and Tentagel((R)) (polymer) were chosen as carriers, attachment occurring via amide-forming coupling or Ru-catalyzed olefin metathesis. Initial lipase inhibition studies are also reported. (C) 2002 Elsevier Science Ltd. All rights reserved.