2-[2-[2-[2-[ethoxy-(4-nitrophenoxy)phosphoryl]ethoxy]ethoxy]ethoxy]ethyl N-prop-2-ynylcarbamate | 1358590-19-8

• 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: 2-[2-[2-[2-[ethoxy-(4-nitrophenoxy)phosphoryl]ethoxy]ethoxy]ethoxy]ethyl N-prop-2-ynylcarbamate
• CAS: 1358590-19-8
• 化学式: C₂₀H₂₉N₂O₁₀P
• 分子量: 488.431
• InChiKey: AXTIQNVRQFGTLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  33
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-[2-[2-[2-[ethoxy-(4-nitrophenoxy)phosphoryl]ethoxy]ethoxy]ethoxy]ethyl N-prop-2-ynylcarbamate 、 在 三(2-羰基乙基)磷盐酸盐 、 copper(II) sulfate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 12.0h， 以28%的产率得到5-[5-[[(2S)-6-[6-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]hexanoylamino]-2-[[4-[5-[4-[[2-[2-[2-[2-[ethoxy-(4-nitrophenoxy)phosphoryl]ethoxy]ethoxy]ethoxy]ethoxycarbonylamino]methyl]triazol-1-yl]pentylamino]-4-oxobutanoyl]amino]hexanoyl]amino]pentylcarbamoyl]-2-[3-(dimethylamino)-6-dimethylazaniumylidenexanthen-9-yl]benzoate
  参考文献：
  名称：

  A para-nitrophenol phosphonate probe labels distinct serine hydrolases of Arabidopsis

  摘要：

  Activity-based protein profiling represents a powerful methodology to probe the activity state of enzymes under various physiological conditions. Here we present the development of a para-nitrophenol phosphonate activity-based probe with structural similarities to the potent agrochemical paraoxon. We demonstrate that this probes labels distinct serine hydrolases with the carboxylesterase CXE12 as the predominant target in Arabidopsis thaliana. The designed probe features a distinct labeling pattern and therefore represents a promising chemical tool to investigate physiological roles of selected serine hydrolases such as CXE12 in plant biology. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.041
• 作为产物：
  描述：

  13,13,14,14-四甲基-3,6,9,12-四氧杂-13-硅-1-十五醇 在 咪唑 、 草酰氯 、 四丁基氟化铵 、 碘 、 碳酸氢钠 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 53.5h， 生成 2-[2-[2-[2-[ethoxy-(4-nitrophenoxy)phosphoryl]ethoxy]ethoxy]ethoxy]ethyl N-prop-2-ynylcarbamate
  参考文献：
  名称：

  A para-nitrophenol phosphonate probe labels distinct serine hydrolases of Arabidopsis

  摘要：

  Activity-based protein profiling represents a powerful methodology to probe the activity state of enzymes under various physiological conditions. Here we present the development of a para-nitrophenol phosphonate activity-based probe with structural similarities to the potent agrochemical paraoxon. We demonstrate that this probes labels distinct serine hydrolases with the carboxylesterase CXE12 as the predominant target in Arabidopsis thaliana. The designed probe features a distinct labeling pattern and therefore represents a promising chemical tool to investigate physiological roles of selected serine hydrolases such as CXE12 in plant biology. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.041

文献信息

• A para-nitrophenol phosphonate probe labels distinct serine hydrolases of Arabidopsis
  作者：Sabrina Nickel、Farnusch Kaschani、Tom Colby、Renier A.L. van der Hoorn、Markus Kaiser

  DOI：10.1016/j.bmc.2011.06.041

  日期：2012.1

  Activity-based protein profiling represents a powerful methodology to probe the activity state of enzymes under various physiological conditions. Here we present the development of a para-nitrophenol phosphonate activity-based probe with structural similarities to the potent agrochemical paraoxon. We demonstrate that this probes labels distinct serine hydrolases with the carboxylesterase CXE12 as the predominant target in Arabidopsis thaliana. The designed probe features a distinct labeling pattern and therefore represents a promising chemical tool to investigate physiological roles of selected serine hydrolases such as CXE12 in plant biology. (C) 2011 Elsevier Ltd. All rights reserved.