2-(diphenylphosphanyl)terephthalic acid 1-methyl ester 4-(N-succinimidyl) ester | 532931-48-9

• 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-(diphenylphosphanyl)terephthalic acid 1-methyl ester 4-(N-succinimidyl) ester
• 英文别名: 1-succinimidyl 3-diphenylphosphino-4-methoxycarbonylbenzoate；succinimidyl-3-diphenylphosphino-4-methoxycarbonylbenzoate；Succinimidyl 3-diphenylphosphino-4-methoxycarbonylbenzoate；4-O-(2,5-dioxopyrrolidin-1-yl) 1-O-methyl 2-diphenylphosphanylbenzene-1,4-dicarboxylate
• CAS: 532931-48-9
• 化学式: C₂₅H₂₀NO₆P
• 分子量: 461.411
• InChiKey: XJSNHTAXBRWNGI-UHFFFAOYSA-N

物化性质

• 熔点：
  151.2-153.6 °C
• 沸点：
  598.4±60.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(diphenylphosphanyl)terephthalic acid 1-methyl ester 4-(N-succinimidyl) ester 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Conversion of Aryl Azides to O-Alkyl Imidates via Modified Staudinger Ligation

  摘要：

  o-Carboalkoxy triarylphosphines are shown to react with aryl azides to provide Staudinger ligation products bearing O-alkyl imidate linkages. This is in contrast to alkyl azides whose ligation to o-carboalkoxy triarylphosphines has been reported to yield amide-linked materials. This extension of the Staudinger ligation for coupling of abiotic reagents under biocompatible conditions highlights the utility of commercially available triarylphosphines through which suitable linkers can be attached via an ester moiety.

  DOI：

  10.1021/ol035635s
• 作为产物：
  描述：

  1-甲基2-碘对苯二甲酸酯 在 palladium diacetate 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 生成 2-(diphenylphosphanyl)terephthalic acid 1-methyl ester 4-(N-succinimidyl) ester
  参考文献：
  名称：

  MASSIVE PARALLEL METHOD FOR DECODING DNA AND RNA

  摘要：

  这项发明提供了一种将核酸连接到固体表面的方法，以及通过在聚合酶反应中将核苷酸类似物并入到DNA增长链中后检测每个核苷酸类似物的身份来测序核酸的方法。该发明还提供了包含独特标签的核苷酸类似物，通过可切割的连接剂连接到核苷酸类似物上，并且包含用于封闭去氧核糖的3′-位置上的—OH基团的可切割化学基团。

  公开号：

  US20160264612A1

文献信息

• [EN] CYANINE DYES AND THEIR CONJUGATES<br/>[FR] COLORANTS À BASE DE CYANINE ET LEURS CONJUGUÉS
  申请人：LI COR INC

  公开号：WO2012054749A1

  公开（公告）日：2012-04-26

  Compounds and methods are disclosed that are useful for noninvasive imaging in the near-infrared spectral range. The cyanine compounds of Formula (I), are presented: wherein Q is a portion of a polymethine bridge selected from the group consisting (Formula (X)). Also included are bioconjugates of the compounds of Formula (I), methods of labeling biomolecules with the compounds, and methods of imaging.

  揭示了用于近红外光谱范围内非侵入性成像的化合物和方法。所述的青菁化合物的化学式（I）如下所示：其中Q是从羧甲纶桥的一部分中选择的，所述羧甲纶桥选自以下群体（化学式（X））。还包括化合物的生物共轭物，用该化合物标记生物分子的方法，以及成像方法。
• Novel bifunctional probe for radioisotope-free photoaffinity labeling: compact structure comprised of photospecific ligand ligation and detectable tag anchoring unitsElectronic supplementary information (ESI) available: Photo-decomposition study of phenyl and benzyl azides. Experimental details for photoreactions of 1 and 5. Synthetic procedures and characterization of new compounds. See http://www.rsc.org/suppdata/ob/b3/b316221d/.
  作者：Takamitsu Hosoya、Toshiyuki Hiramatsu、Takaaki Ikemoto、Masayuki Nakanishi、Hiroshi Aoyama、Ayako Hosoya、Tomoya Iwata、Kei Maruyama、Makoto Endo、Masaaki Suzuki

  DOI：10.1039/b316221d

  日期：——

  A novel method for radioisotope-free photoaffinity labeling was developed, in which a bifunctional ligand is connected to a target protein by activation of a photoreactive group, such as an aromatic azido or 3-trifluoromethyl-3H-diazirin-3-yl group, and identification of the ligated product is achieved by anchoring of a detectable tag through the Staudinger-Bertozzi reaction with an alkyl azido moiety

  开发了一种无放射性同位素的光亲和标记的新方法，其中双功能配体通过激活光反应性基团（例如芳族叠氮基或3-三氟甲基-3H-二氮杂-3-基）与靶蛋白连接，并且通过Staudinger-Bertozzi反应与可在光解中幸存的烷基叠氮基部分锚定可检测标签，可实现对连接产物的鉴定。该方法的化学基础已通过使用具有双官能团的模型化合物在光辐射下，存在用于反应性中间体的捕集剂的条件下进行了确认。该方法的实用性已经通过人HMG-CoA还原酶的催化部分的特异性标记得到证明。
• Capture-Tag-Release: A Strategy for Small Molecule Labeling of Native Enzymes
  作者：Aaron R. Van Dyke、Lily S. Etemad、Michael J. Vessicchio、George A. Naclerio、Victoria Jedson

  DOI：10.1002/cbic.201600267

  日期：2016.9.2

  Capture, tag and release: We report a method for tagging native enzymes with small molecules, by exploiting both the coupling and fragmentation properties of the Staudinger ligation. As a proof‐of‐principle, this strategy was applied to the enzyme β‐galactosidase. Importantly, inhibitor release in the final step restored enzyme activity.

  捕获，标记和释放：我们报告了一种利用小分子Staudinger连接的偶联和片段化特性来标记小分子天然酶的方法。作为原理的证明，该策略被应用于β-半乳糖苷酶。重要的是，抑制剂在最后一步的释放恢复了酶的活性。
• [EN] TARGETED MOLECULAR IMAGING CONTRAST AGENTS<br/>[FR] AGENTS DE CONTRASTE POUR UNE IMAGERIE MOLÉCULAIRE CIBLÉE
  申请人：UNIV MCMASTER

  公开号：WO2015117235A1

  公开（公告）日：2015-08-13

  Novel ultrasound contrast agents are provided which are covalently linked to a bioorthogonal reactive group, and optionally further coupled to a corresponding bioorthogonal reactive group coupled with a targeting entity. Methods for targeted ultrasound imaging using such contrast agents are also provided comprising the steps of: 1) injecting the contrast agent into a patient and imaging the patient at a site of interest to detect the contrast agent, wherein the detection of the contrast agent indicates the presence of a target within the patient.

  提供了新型超声造影剂，其与生物正交反应基团共价连接，并可选择性地进一步耦合到与靶向实体耦合的相应生物正交反应基团上。还提供了使用这种造影剂进行靶向超声成像的方法，包括以下步骤：1）将造影剂注入患者并在感兴趣的部位成像以检测造影剂，其中检测到造影剂表示患者体内存在目标。
• Chemically-selective surface glyco-functionalization of liposomes through Staudinger ligation
  作者：Hailong Zhang、Yong Ma、Xue-Long Sun

  DOI：10.1039/b822420j

  日期：——

  An efficient and chemoselective liposome surface glyco-functionalization method has been developed based on Staudinger ligation, in which the carbohydrate derivative carrying an azide spacer is conjugated onto the surface of preformed liposomes bearing a terminal triphosphine in PBSbuffer (pH 7.4) at room temperature.

  我们在施陶丁格连接法的基础上开发了一种高效的化学选择性脂质体表面糖功能化方法，即在室温下，在 PBS 缓冲液（pH 值为 7.4）中，将带有叠氮化物间隔的碳水化合物衍生物连接到带有末端三膦的预成形脂质体表面。