di-o-nitrobenzyl pyrophosphate | 56883-16-0

• 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: di-o-nitrobenzyl pyrophosphate
• 英文别名: bis(2-nitrobenzyl) hydrogen phosphate；di(2-nitrobenzyl) phosphate；Bis[(2-nitrophenyl)methyl] hydrogen phosphate
• CAS: 56883-16-0
• 化学式: C₁₄H₁₃N₂O₈P
• 分子量: 368.24
• InChiKey: ABAGYLSQOYBDFL-UHFFFAOYSA-N

物化性质

• 熔点：
  98 °C
• 沸点：
  549.4±60.0 °C(Predicted)
• 密度：
  1.527±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  di-o-nitrobenzyl pyrophosphate 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (S)-allyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(7-(bis(2-nitrobenzyloxy)-phosphoryloxy)-8-formyl-2-oxo-2H-chromen-4-yl)propanoate
  参考文献：
  名称：

  A self-immobilizing and fluorogenic unnatural amino acid that mimics phosphotyrosine

  摘要：

  本研究报道了第一种模拟磷酸酪氨酸（pTyr）的自固定、含氟非天然氨基酸的合成。通过使用固相肽合成技术，这种氨基酸随后被纳入肽基探针，并在生物成像和荧光激活细胞分拣（FACS）中得到应用。

  DOI：

  10.1039/c1cc14653j
• 作为产物：
  描述：

  邻硝基苯甲醇 在 吡啶 、 phosphorodichloridic acid 作用下， 以63%的产率得到di-o-nitrobenzyl pyrophosphate
  参考文献：
  名称：

  使用荧光淬灭活性探针 (qABP) 对活细胞中的酶活性进行多色、单光子和双光子成像

  摘要：

  荧光成像提供了一种不可或缺的方式来定位和监测复杂和动态细胞内环境中的生物目标。在目前可用的各种成像剂中，基于小分子的探针为活细胞成像提供了强大的工具，主要是因为它们具有理想的特性，包括细胞渗透性（由于其较小的尺寸）、化学易处理性（例如，不同的分子结构） /designs 可以安装），以及对各种生物事件进行成像的适应性。除了少数例外，大多数现有的小分子探针不适用于体内生物成像实验，其中需要对酶活性和定位进行高分辨率研究。在这篇文章中，我们报道了一类新的高度模块化的荧光猝灭活性探针（qABPs），并且能够以良好的空间和时间分辨率灵敏地成像（通过导致荧光信号放大的多个酶周转）活哺乳动物细胞中不同类型的酶活性。我们还在模块化探针设计中加入了双光子染料，首次实现了酶活性的基于活性的荧光双光子成像。因此，这扩展了目前可用于活细胞生物成像实验的“智能”响应探针的全部内容。酶活性的荧光双光子成像。因此，这

  DOI：

  10.1021/ja200808y

文献信息

• Nitrobenzyl-Based Photosensitive Phosphoramide Mustards:  Synthesis and Photochemical Properties of Potential Prodrugs for Cancer Therapy
  作者：Robert Reinhard、Brigitte F. Schmidt

  DOI：10.1021/jo961861m

  日期：1998.4.1

  their absorption spectra maximum compared to the parent nitrobenzyl moiety. As seen by UV and (31)P NMR spectroscopy, the phosphoramide mustard was quickly liberated upon irradiation with mercury arc lamps. Assaying the structurally different prodrugs on their alkylating activity showed that compounds 13b and 14, derived from secondary benzyl alcohols, are promising prodrug candidates. Their water

  合成了几种基于硝基苄基的光敏磷酰胺芥末。硝基苄基部分在结构上有所不同，以找到关于光释放和烷基化物质活性的最有前途的候选药物。这些化合物的合成被证明甚至对于具有附加功能性的化合物也是适用的。与母体硝基苄基部分相比，目标分子13a，b至14在其最大吸收光谱中表现出预期的红移。如通过UV和（31）P NMR光谱所见，在用汞弧光灯照射时，磷酰胺芥末被快速释放。对结构上不同的前药的烷基化活性进行分析表明，衍生自仲苄醇的化合物13b和14是有前途的候选药物。
• A novel method for phosphodiester and internucleotide bond synthesis
  作者：M. Rubinstein、A. Patchornik

  DOI：10.1016/0040-4020(75)80203-1

  日期：1975.1

  phosphate diesters from various alcohols and nucleosides is described, using the N-methylpyridinium salt of dichlorophosphoric acid (1) as a phosphorylating agent. Internucleotide bonds are formed by stepwise addition of two suitably protected nucleosides to 1. Side products, usually formed during oligonucleotide synthesis were not observed using this new method. In addition, a nucleoside 2′, 3′-cyclic

  描述了使用二氯磷酸的N-甲基吡啶盐（1）作为磷酸化剂，由各种醇和核苷合成磷酸二酯。通过将两个适当保护的核苷逐步加成至1形成核苷酸间键。使用这种新方法未观察到通常在寡核苷酸合成过程中形成的副产物。另外，通过对在5'-羟基处被保护的核糖核苷进行一步磷酸化来制备核苷2'，3'-环状磷酸酯。通过简单的分离方法以相对高的产率分离出产物。
• Catalytic Lewis acid phosphorylation with pyrophosphates
  作者：Owen S. Fenton、Emily E. Allen、Kyle P. Pedretty、Sean D. Till、Joseph E. Todaro、Bianca R. Sculimbrene

  DOI：10.1016/j.tet.2012.08.070

  日期：2012.11

  We report a method for the Lewis acid catalyzed phosphorylation of alcohols with pyrophosphates. Ti((OBu)-Bu-t)(4) was found to be the most effective catalyst in the phosphorylation of both primary and secondary alcohols with tetrabenzylpyrophosphate, providing conversions between 54% and >98% and isolated yields between 50% and 97%. Other pyrophosphates with orthogonal protecting groups were synthesized and screened to validate the generality of the approach. This study will describe how benzyl, methyl, ethyl, allyl, and o-nitrobenzyl pyrophosphates are all effective phosphorylating agents under Lewis acid catalysis. (C) 2012 Elsevier Ltd. All rights reserved.
• Organelle-Specific Detection of Phosphatase Activities with Two-Photon Fluorogenic Probes in Cells and Tissues
  作者：Lin Li、Jingyan Ge、Hao Wu、Qing-Hua Xu、Shao Q. Yao

  DOI：10.1021/ja3036256

  日期：2012.7.25

  Two-photon fluorescence microscopy (TPFM) provides key advantages over conventional fluorescence imaging techniques, namely, increased penetration depth, lower tissue autofluorescence and self-absorption, and reduced photodamage and photobleaching and therefore is particularly useful for imaging deep tissues and animals. Enzyme-detecting, small molecule probes provide powerful alternatives over conventional fluorescent protein (FP) based methods in bioimaging, primarily due to their favorable photophysical properties, cell permeability, and chemical tractability. In this article, we report the first fluorogenic, small molecule reporter system (Y2/Y1) capable of imaging endogenous phosphatase activities in both live mammalian cells and Drosophila brains. The one and two photon excited photophysical properties of the system were thoroughly investigated, thus confirming the system was indeed a suitable Turn-ON fluorescence pair for TPFM. To our knowledge, this is the first enzyme reporting two-photon fluorescence bioimaging system which was designed exclusively from a centrosymmetric dye possessing desirable two-photon properties. By conjugation of our reporter system to different cell penetrating peptides (CPPs), we were able to achieve organelle- and tumor cell specific imaging of phosphatase activities with good spatial and temporal resolution. The diffusion problem typically associated with most small molecule imaging probes was effectively abrogated. We further demonstrated this novel two photon system could be used for imaging endogenous phosphatase activities in Drosophila brains with a detection depth of >100 mu m.