2-(2-(2-(2-(diethoxyphosphoryl)ethoxy)ethoxy)ethoxy)ethyl (2,5-dioxopyrrolidin-1-yl) carbonate | 338964-04-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 2-(2-(2-(2-(diethoxyphosphoryl)ethoxy)ethoxy)ethoxy)ethyl (2,5-dioxopyrrolidin-1-yl) carbonate
• 英文别名: 2-(2-(2-(2-(diethoxyphosphoryl)ethoxy)ethoxy)ethoxy)ethyl (2,5-dioxopyrrolidin-1-yl)carbonate
• CAS: 338964-04-8
• 化学式: C₁₇H₃₀NO₁₁P
• 分子量: 455.399
• InChiKey: WQSYEHXMFBPHJA-UHFFFAOYSA-N

物化性质

• 沸点：
  541.8±60.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  30.0
• 可旋转键数：
  17.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  136.13
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-(2-(2-(2-(diethoxyphosphoryl)ethoxy)ethoxy)ethoxy)ethyl (2,5-dioxopyrrolidin-1-yl) carbonate 在 草酰氯 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-(2-(2-(2-(chloro(ethoxy)phosphoryl)ethoxy)ethoxy)ethoxy)ethyl prop-2-yn-1-ylcarbamate
  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：

  diethyl (2,2,3,3-tetramethyl-4,7,10,13-tetraoxa-3-silapentadecan-15-yl)phosphonate 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-(2-(2-(2-(diethoxyphosphoryl)ethoxy)ethoxy)ethoxy)ethyl (2,5-dioxopyrrolidin-1-yl) carbonate
  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

• An improved synthesis of a fluorophosphonate–polyethylene glycol–biotin probe and its use against competitive substrates
  作者：Hao Xu、Hairat Sabit、Gordon L Amidon、H D Hollis Showalter

  DOI：10.3762/bjoc.9.12

  日期：——

  markedly increases the efficiency of the probe synthesis and overcomes several problems of a prior synthesis. As a proof of principle, FP-PEG-biotin was evaluated against isolated protein mixtures and different rat-tissue homogenates, showing its ability to specifically target serine hydrolases. We also assessed the ability of FP-PEG-biotin to compete with substrates that have high enzyme turnover rates. The

  连接到生物素标签的氟膦酸盐 (FP) 部分是一种原型化学探针，用于通过称为基于活性的蛋白质分析 (ABPP) 的方法定量分析和富集复杂蛋白质组中的活性丝氨酸水解酶。在这项研究中，我们设计了一种新的合成路线，以通过聚乙二醇将已知的 FP 探针连接到生物素标签 (FP-PEG-生物素)。我们的路线显着提高了探针合成的效率并克服了先前合成的几个问题。作为原理证明，针对分离的蛋白质混合物和不同的大鼠组织匀浆对 FP-PEG-生物素进行了评估，显示了其特异性靶向丝氨酸水解酶的能力。我们还评估了 FP-PEG-生物素与具有高酶周转率的底物竞争的能力。
• A molecular Fe-complex as a catalyst probe for in-gel visual detection of proteins via signal amplification
  作者：Sushma Kumari、Chakadola Panda、Shyamalava Mazumdar、Sayam Sen Gupta

  DOI：10.1039/c5cc04399a

  日期：——

  We report the use of a molecular peroxidase mimic biuret FeTAML for chemoselective labeling of proteins and the subsequent visual detection (<0.1 pmoles) of the conjugate in a polyacrylamide gel by catalytic signal amplification.

  我们报告了使用分子过氧化物酶模拟物生物尿素FeTAML对蛋白质进行化学选择性标记，并通过催化信号放大在聚丙烯酰胺凝胶中对共轭物进行可视检测（<0.1皮摩尔）。