2-(diphenylphosphino)terephthalic acid 1-methyl 4-pentafluorophenyl diester | 932710-65-1

• 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-(diphenylphosphino)terephthalic acid 1-methyl 4-pentafluorophenyl diester
• 英文别名: 1-Methyl-4-(pentafluorophenyl)-2-(diphenylphosphino)-1,4-benzenedicarboxylate；1-O-methyl 4-O-(2,3,4,5,6-pentafluorophenyl) 2-diphenylphosphanylbenzene-1,4-dicarboxylate
• CAS: 932710-65-1
• 化学式: C₂₇H₁₆F₅O₄P
• 分子量: 530.387
• InChiKey: OURNVXDJALDDIG-UHFFFAOYSA-N

物化性质

• 熔点：
  109-111°C
• 沸点：
  604.7±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(diphenylphosphino)terephthalic acid 1-methyl 4-pentafluorophenyl diester 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  使用生物正交化学报告基因对细胞表面聚糖进行成像

  摘要：

  生物分子在生命系统中发挥作用时的可视化对于理解复杂的生物过程非常重要。在这里，我们应用生物正交化学报告技术使用多种代谢标签对细胞表面聚糖进行成像。我们将两种不同的化学报告基因引入唾液酸和 N-乙酰半乳糖胺 (GalNAc) 残基，然后用荧光探针同时对它们相关的细胞表面聚糖进行成像。

  DOI：

  10.1021/ja070238o
• 作为产物：
  描述：

  三氟乙酸五氟苯酯 、 3-(二苯基膦基)-4-(甲氧基羰基)苯甲酸 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以69%的产率得到2-(diphenylphosphino)terephthalic acid 1-methyl 4-pentafluorophenyl diester
  参考文献：
  名称：

  DNA杂交编码的可编程细胞粘附。

  摘要：

  DOI：

  10.1002/anie.200502421

文献信息

• Selective enrichment and identification of azide-tagged cross-linked peptides using chemical ligation and mass spectrometry
  作者：Danielle Vellucci、Athit Kao、Robyn M. Kaake、Scott D. Rychnovsky、Lan Huang

  DOI：10.1016/j.jasms.2010.04.004

  日期：2010.8.1

  Protein-protein interaction is one of the key regulatory mechanisms for controlling protein function in various cellular processes. Chemical cross-linking coupled with mass spectrometry has proven to be a powerful method not only for mapping protein-protein interactions of all natures, including weak and transient ones, but also for determining their interaction interfaces. One critical challenge remaining

  蛋白质-蛋白质相互作用是控制各种细胞过程中蛋白质功能的关键调节机制之一。化学交联与质谱联用已被证明是一种强大的方法，不仅用于绘制所有性质的蛋白质 - 蛋白质相互作用，包括弱和瞬态相互作用，而且还用于确定它们的相互作用界面。这种方法剩下的一个关键挑战是如何有效地从复杂的肽混合物中分离和鉴定交联产物。在这项工作中，我们开发了一种使用共轭化学选择性富集交联产物的新策略。设计并合成了叠氮化物标记的交联剂和两种生物素化偶联试剂。模型肽和细胞色素c 的交联以及对所得交联肽的富集进行了评估。已经使用两种策略证明了叠氮化物标记的交联肽的选择性缀合：铜催化环加成和施陶丁格连接。虽然这两种方法都有效，但 Staudinger 连接更适合富集交联肽，因为样品处理问题较少。LC MS n分析结合使用 Protein Prospector 软件包进行数据库搜索，可识别 58 种细胞色素c富集和亲和纯化后的交联肽。这项工作中开发的新富集策略为促进通过
• Targeted and armed oncolytic adenovirus via chemoselective modification
  作者：Partha S. Banerjee、Edison S. Zuniga、Iwao Ojima、Isaac S. Carrico

  DOI：10.1016/j.bmcl.2011.05.039

  日期：2011.9

  Oncolytic adenoviruses (Ads) are an emerging alternative therapy for cancer; however, clinical trial have not yet demonstrated sufficient efficacy. When oncolytic Ads are used in combination with taxoids a synergistic increase in both cytotoxicity and viral replication is observed. In order to generate a next generation oncolytic adenovirus, virion were physically conjugated to a highly potent taxoid, SB-T-1214, and a folate targeting motif. Conjugation was enabled via the metabolic incorporation of non-canonical monosaccharides (O-GlcNAz) and amino acids (homopropargylglycine), which served as sites for chemoselective modification. (C) 2011 Elsevier Ltd. All rights reserved.
• Smart tools and orthogonal click-like reactions onto small unilamellar vesicles
  作者：Christophe Salomé、Maria Vittoria Spanedda、Benoit Hilbold、Etienne Berner、Béatrice Heurtault、Sylvie Fournel、Benoit Frisch、Line Bourel-Bonnet

  DOI：10.1016/j.chemphyslip.2015.03.004

  日期：2015.5

  Click-based reactions were conducted at the surface of small unilamellar vesicles (SUVs) to provide onto-vesicle chemistry with efficient innovative ready-for-use tools. For that purpose, four amphiphilic molecules were designed to insert into bilayers while presenting a reactive functional head. In this manner, a dioleylglycero-ethoxy-ethoxy-ethoxy-ethanamine (DOG-PEG(4)-NH2) was chosen as a common platform while the reactive amine head was converted into several electrophilic functions. Thus, two dioleylglycerol-based cyclooctyne anchors were prepared: cyclooct-1-yn-3-glycolic acid-based anchor (DOG-COA) and 1-fluorocyclooct-2-ynecarboxylic acid-based anchor (DOG-FCOA). The last one differed from the first one in that a fluorine atom reinforces the electrophilic properties of the unsaturated bond. In addition, a third dioleylglycerol-based triphenylphosphine (DOG-PPh3) was synthesized for the first time. These three innovative amphiphilic anchors were designed to react with any azide-based biomolecule following copper-free Huisgen 1,4-cycloaddition and Staudinger ligation, respectively. A fourth anchor bearing a 3,4-dibromomaleimide ring (DOG-DBM) was also unprecedentedly synthesized, to be further substituted by two thiols. Model reactions conducted in solution with either model biotinyl azide or model biotinyl disulfide gave good to total conversions and excellent isolated yields. The four new anchors were inserted into SUVs whose formula is classically used in in vivo biology. Stability and surface overall electrostatic charge were in the expected range and constant over the study. Then, the functionalized liposomes were ligated to biotin-based reagents and the experimental conditions were finely tuned to optimize the conversion. The biotinyl liposomes were demonstrated functional and totally accessible in an affinity test based on biotin scaffold quantification. Finally, DOG-FCOA's reactivity was confronted to that of DOG-DBM in a 'one-pot' orthogonal reaction. (Biotin-S)(2) and TAMRA-N-3 (tetramethylcarboxyrhodamine azide) were successively conjugated to the liposome suspension in a successful manner. These data implement and reinforce the interest of bioorthogonal click-like reactions onto lipid nanoparticles. (C) 2015 Elsevier Ireland Ltd. All rights reserved.
• Light-Activated Staudinger–Bertozzi Ligation within Living Animals
  作者：Lisa Shah、Scott T. Laughlin、Isaac S. Carrico

  DOI：10.1021/jacs.5b13401

  日期：2016.4.27

  The ability to regulate small molecule chemistry in vivo will enable new avenues of exploration in imaging and pharmacology. However, realization of these goals will require reactions with high specificity and precise control. Here we demonstrate photocontrol over the highly specific Staudinger-Bertozzi ligation in vitro and in vivo. Our simple approach, photocaging the key phosphine atom, allows for the facile production of reagents with photochemistry that can be engineered for specific applications. The resulting compounds, which are both stable and efficiently activated, enable the spatial labeling of metabolically introduced azides in vitro and on live zebrafish.
• Synthesis of transferrin (Tf) conjugated liposomes via Staudinger ligation
  作者：Songlin Xu、Ying Liu、Heng-Chiat Tai、Jing Zhu、Hong Ding、Robert J. Lee

  DOI：10.1016/j.ijpharm.2010.10.053

  日期：2011.2

  Staudinger ligation was evaluated as a strategy for synthesizing receptor targeted liposomes. First, an activated lipid derivative was synthesized by reacting dioleoyl phosphatidylethanolamine (DOPE) and 2-(diphenylphosphino) terephthalic acid 1-methyl 4-penta-fluorophenyldiester. Second, transferrin (TO was activated with p-azidophenyl isothiocyanate. Third, liposomes containing the activated lipid were prepared and then coupled to the activated Tf via the Staudinger reaction. These liposomes were evaluated in KB cells for cellular uptake and cytotoxicity, and in mice for pharmacokinetic properties. Tf-derivatized liposomes encapsulating calcein prepared by this conjugation method effectively targeted Tf receptor expressing KB cells. In addition, the Tf-targeted liposomes entrapping doxorubicin showed greatly enhanced in vitro cytotoxicity relative to non-targeted control liposomes. Pharmacokinetic parameters indicated that these liposomes retained long circulating properties relative to the free drug. In summary, Staudinger ligation is an effective method for the synthesis of receptor targeted liposomes. (C) 2010 Elsevier B.V. All rights reserved.